Researcher basic information

• 博士（理学）, 東京工業大学
• 理学修士, 東京工業大学

• https://researchmap.jp/read0008460?lang=en

• https://orcid.org/0000-0002-0580-0125
• https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200901026503101502
• https://wwwchem.sci.hokudai.ac.jp/~oc2/
• http://barato.sci.hokudai.ac.jp/~oc2/

• https://orcid.org/0000-0002-0580-0125

• 200901026503101502

• 合成化学
• 全合成
• 反応開発
• 有機合成

• Nanotechnology/Materials, Synthetic organic chemistry
• Life Science, Bioorganic chemistry
• Nanotechnology/Materials, Structural organic chemistry and physical organic chemistry

• Bachelor's degree program, School of Science
• Master's degree program, Graduate School of Chemical Sciences and Engineering
• Doctoral (PhD) degree program, Graduate School of Chemical Sciences and Engineering

Research activity information

• 2013, The Chemical Society of Japan, Award for Creative Work
  谷野 圭持
• 2011, Nagoya Silver Medal
  TANINO Keiji, Japan
• 2007, The Society of Synthetic Organic Chemistry, Japan, Mukaiyama Award
  Japan
• 2000, The Society of Synthetic Organic Chemistry, Japan, Incentive Award in Synthetic Organic Chemistry
  Japan

• A Radical-Based Construction of the Khayanolide Tetracyclic Framework Enabled by a Cyclization Cascade and Alcohol-Mediated Hydrogen Atom Transfer
  Kosuke Odagiri; Kosaku Horiguchi; Takahiro Suzuki; Junya Takino; Keiji Tanino
  Organic Letters, 19 Jun. 2026, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Discovery of Hatching Stimulants for Globodera pallida with Simple Chemical Structures and Their Application for Nematode Density Reduction in Soil
  Atsuhiko Kushida; Jun Kanazawa; Itaru Sakata; Yuto Ikeda; Takashi Kitayama; Kosuke Kato; Takuya Itabashi; Yuki Sugimoto; Satoshi Koizumi; Yoko Osawa; Tsutomu Inoue; Keiji Tanino
  Plant Disease, Scientific Societies, 27 Mar. 2026, [Peer-reviewed], [Last author]
  English, Scientific journal, Potato cyst nematodes (PCN), Globodera pallida and G. rostochiensis, are among the most destructive pests affecting potatoes. Hatching stimulants that induce “suicide hatching” in the absence of host plants offer a promising strategy for PCN management. However, previously identified natural hatching stimulants have complex structures, making them difficult to synthesize. Therefore, we explored hatching stimulants with simple structures to develop an effective method for PCN control. We screened 9,600 compounds and identified 9 with weak G. pallida hatching-stimulation activity. To further the search, we examined 191 commercially available compounds that shared structural similarities with these nine compounds, and discovered a compound (5,5-dimethyl-4-phenylpyrrolidin-2-one) that induced an 89% hatching rate in G. pallida juveniles at a concentration of 10 μg/ml. Further synthesis of structurally related compounds yielded several compounds that promoted high hatching rates of the nematode, including three substances that induced over 90% hatch at 10 ng/ml. However, these compounds did not stimulate hatching in G. rostochiensis. Structure-activity analysis suggested that the 5-membered ring with substituted phenyl, dimethyl, and carbonyl groups, characteristic of 5,5-dimethyl-4-phenylpyrrolidin-2-one, was crucial for hatching activity. Application of the active compound 5,5-dimethyl-4-(p-tolyl)pyrrolidin-2-one at 30 mg/m ² in a G. pallida-infested field reduced the nematode egg density in the soil by approximately 90%. These compounds with simple structures hold great potential as effective control agents for G. pallida.
• Total Synthesis of (±)‐Cristaxenicin A: Construction of Nine‐Membered Ring by Eschenmoser–Claisen/Cope Rearrangement Cascade
  Wataru Kiuchi; Yuko Tsunoda; Kentaro Ishikura; Kosuke Kato; Junya Takino; Takahiro Suzuki; Keiji Tanino
  Angewandte Chemie International Edition, 16 Feb. 2026, [Peer-reviewed], [Last author, Corresponding author], [International Magazine]
  English, Scientific journal
• Total Synthesis of (±)‐Cristaxenicin A: Construction of Nine‐Membered Ring by Eschenmoser–Claisen/Cope Rearrangement Cascade
  Wataru Kiuchi; Yuko Tsunoda; Kentaro Ishikura; Kosuke Kato; Junya Takino; Takahiro Suzuki; Keiji Tanino
  Angewandte Chemie, 16 Feb. 2026, [Peer-reviewed], [Last author, Corresponding author]
  German, Scientific journal
• Synthesis of Seven-Membered Nitriles by Formal Anionic Divinylcyclopropane Rearrangement
  Takashi Takeuchi; Yuki Yukutake; Junya Takino; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 27, 51, 14259, 14263, American Chemical Society (ACS), 15 Dec. 2025, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Two-step transformation of ketones to carboxylic acids through a ring-opening reaction of epoxynitriles with a squarate anion
  Tomoyuki Fujita; Kazuto Sato; Takahiro Suzuki; Kazutada Ikeuchi; Keiji Tanino
  Chemistry Letters, 54, 11, Oxford University Press (OUP), 28 Oct. 2025, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, Abstract
  
  Herein, we describe a new method to convert epoxynitriles, which can be synthesized from ketones via the Darzens condensations, into carboxylic acids using a squaric acid and 1,8-diazabicyclo[4.3.0]undec-7-ene. The epoxide ring is opened via nucleophilic attack by the squarate anion, prepared in situ, at the sterically less hindered site of the epoxide moiety, and the resulting intermediate is transformed into an acyl cyanide, which is subjected to basic hydrolysis to afford the corresponding carboxylic acids.
• Synthesis of Cyclobuta[cd]pentalenes via an Intramolecular Double Michael Addition Reaction of 1,3-Cyclopentanedione Derivatives
  Makoto Kobayashi; Misora Ono; Tomonari Sasage; Yuma Yamazaki; Takahiro Suzuki; Keiji Tanino; Seiichi Nakamura; Naoki Kanoh; Kazutada Ikeuchi
  Organic Letters, 27, 33, 9341, 9346, 22 Aug. 2025, [Peer-reviewed]
  English, Scientific journal, 50783804
• Solanoeclepin C, a root‐secreted molecule converted by rhizosphere microbes to hatching factors for potato cyst nematodes
  Ryota Akiyama; Yui Kawano; Kosuke Shimizu; Soichiro Makino; Karen Akanuma; Haru Nagatomo; Masami Yokota Hirai; Yukihiro Sugimoto; Atsuhiko Kushida; Keiji Tanino; Masaharu Mizutani
  New Phytologist, 247, 3, 1370, 1381, Wiley, 26 May 2025, [Peer-reviewed]
  English, Scientific journal, Summary
  
  Eclepins are root‐secreted compounds that induce the hatching of cyst nematodes. Solanoeclepin A (SEA) and B (SEB) have been isolated as potent hatching factors for potato cyst nematodes (PCNs). SEB is biosynthesized in roots, released into the rhizosphere, and converted into SEA by soil microorganisms. However, given that SEB and SEA exhibit comparable hatching‐inducing activity toward PCNs, the ecological significance of microbial solanoeclepin metabolism in eclepin‐mediated communication remains unclear.
  
  In this study, we identified solanoeclepin C (SEC), a previously unrecognized solanoeclepin secreted by tomato and potato roots. Structural analysis revealed that SEC is an acetylated derivative of SEB. Soil incubation experiments demonstrated that SEC is converted into SEB and subsequently into SEA. SEC exhibits  10 000‐fold lower hatching‐inducing activity than SEA.
  
  Gene expression analysis in hydroponically grown tomatoes showed that solanoeclepin biosynthesis is upregulated under nitrogen and phosphorus deficiencies, with nitrogen starvation having the strongest effect.
  
  Our results demonstrate that although SEC itself exhibits low hatching‐inducing activity, it is converted by soil microorganisms into SEB and SEA, which are then exploited by PCNs to trigger their hatching. These findings reveal a previously unrecognized three‐way interaction among plants, soil microbes, and nematodes mediated by solanoeclepins.
• Remodelling of tricyclic carbon frameworks with a norbornene scaffold
  Akihiro Yoshitani; Tomonari Sasage; Ranmaru Kato; Takahiro Suzuki; Kazutada Ikeuchi; Keiji Tanino
  Chemical Communications, 61, 84, 16372, 16375, Royal Society of Chemistry (RSC), 2025, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, We herein describe a facile method to remodel tricyclic carbon frameworks via Pd(ii)-mediated activation of double bonds in norbornene scaffolds, followed by consecutive C–C cross-coupling reactions of the resulting Pd-alkyl intermediates.
• Unique Reactivity of the 1,4‐Bis(silyloxy)‐1,3‐cyclopentadiene Moiety: Application to the Synthesis of 7‐Norbornanone Derivatives
  Kazutada Ikeuchi; Yoshito Hirokawa; Tomonari Sasage; Ryo Fujii; Akihiro Yoshitani; Takahiro Suzuki; Keiji Tanino
  Chemistry – A European Journal, 19 Aug. 2024, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons
  Takahiro Suzuki; Kotaro Yamashita; Wataru Ikeda; Kazutada Ikeuchi; Keiji Tanino
  Asian Journal of Organic Chemistry, Wiley, 24 Jul. 2024, [Peer-reviewed], [Last author]
  English, Scientific journal, Abstract
  
  Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5‐ or 6‐exo‐trig/5‐exo‐dig reactions triggered by epoxide ring opening with Cp₂TiCl were found to provide a useful unified synthetic method for generating the carbon skeletons of clovane and cedrane, two tricyclic sesquiterpenes. The factors responsible for the development of stereoselectivity during cyclization are also discussed.
• A Journey to the Total Synthesis of Brasilicardins
  Ryusei Itoh; Keiji Tanino; Fumihiko Yoshimura
  Modern Natural Product Synthesis, 28 May 2024, [Peer-reviewed]
  English, AbstractC(sp3)-rich natural products with quaternary carbon stereocenters have recently received increasing attention as formidable synthetic targets and higher lead and drug compounds. Among them, brasilicardins, which are terpenoids–amino acids–saccharide(s) hybrids, share a unique and highly strained anti-syn-anti-fused 6,6,6-tricyclic terpenoid skeleton containing two adjacent quaternary carbon stereocenters and have attracted attention as promising immunosuppressive drug lead compounds. Herein, we describe our endeavor toward a unified total synthesis of brasilicardins A–D, focusing on overcoming various synthetic challenges. In addition, we discuss several key lessons learned from our journey.
• Synthesis of dihydrotropone derivatives using an anionic 8π-electrocyclic reaction
  Ranmaru Kato; Takahiro Suzuki; Keiji Tanino
  Chemical Communications, 60, 52, 6619, 6622, Royal Society of Chemistry (RSC), 2024, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, A new method to synthesise functionalised cycloheptatrienes was established using the anionic 8π-electrocyclic reaction of β-ketoester-derived dienyne substrates.
• Alcohol synthesis based on the S_N2 reactions of alkyl halides with the squarate dianion
  Kazuto Sato; Tomoyuki Fujita; Takashi Takeuchi; Takahiro Suzuki; Kazutada Ikeuchi; Keiji Tanino
  Organic & Biomolecular Chemistry, 22, 7, 1369, 1373, Royal Society of Chemistry (RSC), 2024, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, We developed a convenient method for transforming alkyl halides into the corresponding alcohols through an S_N2 reaction using the squarate anion, prepared from squaric acid and a base, followed by a one-pot hydrolysis of the resulting squaric esters.
• Solanoeclepin B, a hatching factor for potato cyst nematode
  Kosuke Shimizu; Ryota Akiyama; Yuya Okamura; Chihiro Ogawa; Yuki Masuda; Itaru Sakata; Bunta Watanabe; Yukihiro Sugimoto; Atsuhiko Kushida; Keiji Tanino; Masaharu Mizutani
  Science Advances, 9, 11, American Association for the Advancement of Science (AAAS), 17 Mar. 2023, [Peer-reviewed]
  English, Scientific journal, The potato cyst nematode (PCN) causes extensive crop losses worldwide. Because the hatching of PCN requires host-derived molecules known as hatching factors (HFs), regulating HF production in host plants may help to control this harmful pest. Solanoeclepin A (SEA), isolated from potato, is the most active HF for PCN; however, its biosynthesis is completely unknown. We discovered a HF called solanoeclepin B (SEB) from potato and tomato root exudates and showed that SEB was biosynthesized in the plant and converted to SEA outside the plant by biotic agents. Moreover, we identified five SEB biosynthetic genes encoding three 2-oxoglutarate-dependent dioxygenases and two cytochrome P450 monooxygenases in tomato. Exudates from tomato hairy roots in which each of the genes was disrupted contained no SEB and had low hatch-stimulating activity for PCN. These findings will help to breed crops with a lower risk of PCN infection.
• Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety
  Kazutada Ikeuchi; Shota Haraguchi; Ryo Fujii; Hidetoshi Yamada; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 25, 16, 2751, 2755, American Chemical Society (ACS), 28 Feb. 2023, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Diastereoselective Synthesis oftrans‐anti‐Hydrophenanthrenes via Ti‐mediated Radical Cyclization and Total Synthesis of Kamebanin
  Takahiro Suzuki; Wataru Ikeda; Ayaka Kanno; Kazutada Ikeuchi; Keiji Tanino
  Chemistry – A European Journal, 29, 17, Wiley, 17 Feb. 2023, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, Abstract
  
  Ent‐kaurenes consist of an ABC‐ring based on atrans‐anti‐hydrophenanthrene skeleton and a D ring with an exomethylene. Highly oxygen‐functionalizedent‐kauren‐15‐ones have promising antiinflammatory pharmacological activity. In this study, we developed a novel diastereoselective synthesis oftrans‐anti‐hydrophenanthrenes via a Ti‐mediated reductive radical cyclization. We also demonstrated the applicability of this method by developing the first total synthesis of (±)‐kamebanin (longest linear sequence; 17 steps, overall yield; 6.5 %). Furthermore, this synthesis provided a formal semi‐pinacol rearrangement for the construction of the quaternary carbon at C8 and a novel Thorpe‐Ziegler‐type reaction for the construction of the D‐ring.
• Synthesis of 2-Alkyl-2-(2-furanyl)-1,3-cyclopentanediones
  Kazutada Ikeuchi; Yusuke Ozoe; Ranmaru Kato; Takahiro Suzuki; Keiji Tanino
  Synthesis, 55, 10, 1525, 1532, Georg Thieme Verlag KG, 27 Dec. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, Abstract
  
  2,2-Disubstituted 1,3-cyclopentanediones are versatile building blocks for synthesizing complex natural products with bicyclic structures including cyclopentane rings. The reported method for the synthesis of these compounds involves the semi-pinacol rearrangement of a Mukaiyama aldol adduct prepared from a ketone/ketal and 1,2-bis(trimethylsilyloxy)cyclobutene. However, the adoption of α-oxy-functionalized ketones/ketals is quite difficult, as demonstrated by our experiments. To overcome this limitation of the method, 2-acylfuran derivatives were used as the reactants to synthesize 2,2-disubstituted 1,3-cyclopentanediones. Furthermore, two reaction conditions, that is, the use of 1.4 equivalents of a boron trifluoride-diethyl ether complex or 0.4 and 0.2 equivalent of trimethylsilyl triflate and methoxytrimethylsilane, respectively, were established for the conversion of 2-acylfurans into the corresponding 1,3-cyclopentanediones in acceptable yields. The transformations of the furan rings in the obtained products were also investigated.
• Total Synthesis and Structural Revision of the 6,11-Epoxyisodaucane Natural Sesquiterpene Using an Anionic 8π Electrocyclic Reaction
  Ranmaru Kato; Hiroki Saito; Kazutada Ikeuchi; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 24, 43, 7939, 7943, American Chemical Society (ACS), 21 Oct. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Lipid Droplet Formation Is Regulated by Ser/Thr Phosphatase PPM1D via Dephosphorylation of Perilipin 1
  Rui Kamada; Sae Uno; Nozomi Kimura; Fumihiko Yoshimura; Keiji Tanino; Kazuyasu Sakaguchi
  International Journal of Molecular Sciences, 23, 19, 12046, 12046, MDPI AG, 10 Oct. 2022, [Peer-reviewed], [International Magazine]
  English, Scientific journal, Hypertrophy and hyperplasia of white adipocytes induce obesity, leading to diseases such as type 2 diabetes and hypertension, and even cancer. Hypertrophy of white adipocytes is attributed to the excessive storage of the energy form of triglycerides in lipid droplets (LDs). LDs are fat storage organelles that maintain whole-body energy homeostasis. It is important to understand the mechanism of LD formation for the development of obesity therapy; however, the regulatory mechanisms of LD size and formation are not fully understood. In this study, we demonstrated that the PPM family phosphatase PPM1D regulates LD formation. PPM1D specific inhibitor, SL-176 significantly decreased LD formation via two different pathways: dependent of and independent of adipocyte-differentiation processes. In the mature white adipocytes after differentiation, LD formation was found to be controlled by PPM1D via dephosphorylation of Ser511 of perilipin 1. We found that inhibition of PPM1D in mature white adipocytes significantly reduced the size of the LDs via dephosphorylation of Ser511 of perilipin 1 but did not change the lipolysis sensitivity and the total amount of lipid in cells. Collectively, the results of this study provide evidence that PPM1D plays an important role in LD formation in mature adipocytes.
• Total Synthesis of 2-Isocyanoallopupukeanane: Construction of Caged Skeleton by Intramolecular Alkylation of Bromonitriles
  Kosuke Kato; Kazutada Ikeuchi; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 24, 35, 6407, 6411, American Chemical Society ({ACS}), 09 Sep. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Two-Step Method for Constructing a Quaternary Carbon Atom with a Geminal Divinyl Group from a Ketone
  Ryota Ogura; Kazuto Satoh; Wataru Kiuchi; Kosuke Kato; Kazutada Ikeuchi; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 24, 28, 5040, 5044, American Chemical Society ({ACS}), 22 Jul. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Model Synthetic Study of Tutin, a Picrotoxane-Type Sesquiterpene: Stereoselective Construction of a cis-Fused 5,6-Ring Skeleton
  Kazutada Ikeuchi; Shota Haraguchi; Hidetoshi Yamada; Keiji Tanino
  Chemical and Pharmaceutical Bulletin, 70, 6, 435, 442, Pharmaceutical Society of Japan, 01 Jun. 2022, [Peer-reviewed]
  English, Scientific journal
• Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-Ring Compound
  Keiji Tanino; Yuki Yukutake; Takahiro Hiramatsu; Ryusei Itoh; Kazutada Ikeuchi; Takahiro Suzuki
  Synlett, 33, 03, 296, 300, Georg Thieme Verlag KG, Feb. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, Abstract
  
  Synthetic studies on an ABC-ring model of tubiferal A, a triterpenoid isolated from the fruit bodies of the Tubifera dimorphotheca myxomycete, are described. The stereogenic centers at the angular positions were constructed through the stereoselective addition of a C-ring allylborane followed by an Eschenmoser–Claisen rearrangement reaction prior to the formation of the AB-ring system by a double intramolecular alkylation reaction of a dichloro nitrile intermediate.
• Synthetic Studies of Daphniphyllum Alkaloids: A New Method for the Construction of [7-5-5] All-Carbon Tricyclic Skeleton
  Keiji Tanino; Jun-ichiro Kishi; Kazutada Ikeuchi; Takahiro Suzuki
  Synlett, 33, 02, 196, 200, Georg Thieme Verlag KG, Jan. 2022, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, Abstract
  
  Daphniphyllum alkaloids have complex molecular structures; consequently, their synthesis can be challenging. A new method for the construction of the [7-5-5] tricyclic core of Daphniphyllum alkaloids was developed. The bicyclo[5.3.0]decane skeleton was constructed through a divinylcyclopropane rearrangement of a cyclopentenone derivative with a vinylcyclopropyl group at the β-position. After introduction of a 2-iodoethyl group by a regioselective Michael addition with phenyl vinyl selenone, the [7-5-5] tricyclic system was formed by intramolecular alkylation of a cyclopentadienyl anion species.
• 8π Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes
  Hiroki Saito; Ranmaru Kato; Kazutada Ikeuchi; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 23, 24, 9606, 9610, American Chemical Society (ACS), 09 Dec. 2021, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels–Alder Reaction
  Kazutada Ikeuchi; Tomonari Sasage; Gen Yamada; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 23, 23, 9123, 9127, American Chemical Society (ACS), 03 Dec. 2021, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• PPM1D Is a Therapeutic Target in Childhood Neural Tumors
  Jelena Milosevic; Diana Treis; Susanne Fransson; Gabriel Gallo-Oller; Baldur Sveinbjörnsson; Nina Eissler; Keiji Tanino; Kazuyasu Sakaguchi; Tommy Martinsson; Malin Wickström; Per Kogner; John Inge Johnsen
  Cancers, 13, 23, 6042, 6042, MDPI AG, 30 Nov. 2021, [Peer-reviewed]
  English, Scientific journal, Childhood medulloblastoma and high-risk neuroblastoma frequently present with segmental gain of chromosome 17q corresponding to aggressive tumors and poor patient prognosis. Located within the 17q-gained chromosomal segments is PPM1D at chromosome 17q23.2. PPM1D encodes a serine/threonine phosphatase, WIP1, that is a negative regulator of p53 activity as well as key proteins involved in cell cycle control, DNA repair and apoptosis. Here, we show that the level of PPM1D expression correlates with chromosome 17q gain in medulloblastoma and neuroblastoma cells, and both medulloblastoma and neuroblastoma cells are highly dependent on PPM1D expression for survival. Comparison of different inhibitors of WIP1 showed that SL-176 was the most potent compound inhibiting medulloblastoma and neuroblastoma growth and had similar or more potent effects on cell survival than the MDM2 inhibitor Nutlin-3 or the p53 activator RITA. SL-176 monotherapy significantly suppressed the growth of established medulloblastoma and neuroblastoma xenografts in nude mice. These results suggest that the development of clinically applicable compounds inhibiting the activity of WIP1 is of importance since PPM1D activating mutations, genetic gain or amplifications and/or overexpression of WIP1 are frequently detected in several different cancers.
• Synthesis of Seven-Membered Cross-Conjugated Cyclic Trienes by 8π Electrocyclic Reaction
  Ranmaru Kato; Hiroki Saito; Shoko Uda; Daisuke Domon; Kazutada Ikeuchi; Takahiro Suzuki; Keiji Tanino
  Organic Letters, 23, 22, 8878, 8882, American Chemical Society ({ACS}), 19 Nov. 2021, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes
  Takahiro Suzuki; Riko Nagahama; Muhammad Aiman Fariz; Yuki Yukutake; Kazutada Ikeuchi; Keiji Tanino
  Organics, 2, 3, 306, 312, MDPI AG, 02 Sep. 2021, [Peer-reviewed], [Last author]
  English, Scientific journal, Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.
• Synthetic Studies on Cyclocitrinol: Construction of the ABC Ring System Based on Epoxy–Nitrile Cyclization
  Keiji Tanino; Kazuto Sato
  Synlett, 32, 07, 674, 678, Georg Thieme Verlag KG, Apr. 2021, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal, The stereoselective synthesis of a model compound containing the ABC ring system of cyclocitrinol was accomplished. After connecting a C ring allyltitanium segment with an A ring bi­cyclo[4.1.0]heptanone segment, the seven-membered B ring moiety was constructed by an intramolecular cyclization reaction of an epoxy nitrile. The enone moiety was introduced through an oxidative decyanation reaction, and the bicyclo[4.4.1]undecane skeleton with the highly strained olefin moiety was formed through a ring-opening reaction of the bicyclo[4.1.0]heptane substructure.
• Biomimetic Total Synthesis of (+)-Chloropupukeananin, (–)-Chloropupukeanolide D, and Chloropestolides
  Takahiro Suzuki; Soichiro Watanabe; Wataru Ikeda; Susumu Kobayashi; Keiji Tanino
  The Journal of Organic Chemistry, 86, 21, 15597, 15605, American Chemical Society ({ACS}), 16 Mar. 2021, [Peer-reviewed], [Last author]
  Scientific journal
• Development of a mugineic acid family phytosiderophore analog as an iron fertilizer
  Motofumi Suzuki; Atsumi Urabe; Sayaka Sasaki; Ryo Tsugawa; Satoshi Nishio; Haruka Mukaiyama; Yoshiko Murata; Hiroshi Masuda; May Sann Aung; Akane Mera; Masaki Takeuchi; Keijo Fukushima; Michika Kanaki; Kaori Kobayashi; Yuichi Chiba; Binod Babu Shrestha; Hiromi Nakanishi; Takehiro Watanabe; Atsushi Nakayama; Hiromichi Fujino; Takanori Kobayashi; Keiji Tanino; Naoko K. Nishizawa; Kosuke Namba
  Nature Communications, 12, 1, 10 Mar. 2021, [Peer-reviewed]
  English, Scientific journal
• The hatching-stimulation activity of solanoeclepin A toward the eggs of Globodera (Tylenchida: Heteroderidae) species
  Itaru Sakata; Atsuhiko Kushida; Keiji Tanino
  Applied Entomology and Zoology, 56, 1, 51, 57, Springer Science and Business Media LLC, Feb. 2021, [Peer-reviewed], [Last author]
  English, Scientific journal
• Chemical Synthesis of Brasilicardins
  Fumihiko Yoshimura; Ryusei Itoh; Makoto Torizuka; Genki Mori; Keiji Tanino
  Journal of Synthetic Organic Chemistry, Japan, 78, 11, 1085, 1093, The Society of Synthetic Organic Chemistry, Japan, 01 Nov. 2020, [Peer-reviewed], [Invited], [Last author, Corresponding author]
  Scientific journal
• Hatching stimulation activity of steroidal glycoalkaloids toward the potato cyst nematode, Globodera rostochiensis
  Kosuke Shimizu; Atsuhiko Kushida; Ryota Akiyama; Hyoung Jae Lee; Yuya Okamura; Yuki Masuda; Itaru Sakata; Keiji Tanino; Seiji Matsukida; Tsutomu Inoue; Yukihiro Sugimoto; Masaharu Mizutani
  Plant Biotechnology, 37, 3, 319, 325, Japanese Society for Plant Cell and Molecular Biology, 25 Sep. 2020, [Peer-reviewed]
  Scientific journal
• Does solanoeclepin A act as a host-searching cue for <i>Globodera rostochiensis</i>?
  Itaru Sakata; Atsuhiko Kushida; Takashi Narabu; Keiji Tanino
  Nematological Research (Japanese Journal of Nematology), 50, 1, 9, 12, The Japanese Nematological Society, 20 Sep. 2020, [Peer-reviewed], [Last author]
  English, Scientific journal
• Formal Total Synthesis of Atropurpuran
  Takahiro Suzuki; Takeshi Koyama; Kenta Nakanishi; Susumu Kobayashi; Keiji Tanino
  The Journal of Organic Chemistry, 85, 15, 10125, 10135, American Chemical Society ({ACS}), 07 Aug. 2020, [Peer-reviewed], [Last author]
  English, Scientific journal
• Development of a 1,3a,6a-triazapentalene derivative as a compact and thiol-specific fluorescent labeling reagent
  Atsushi Nakayama; Akira Otani; Tsubasa Inokuma; Daisuke Tsuji; Haruka Mukaiyama; Akira Nakayama; Kohji Itoh; Akira Otaka; Keiji Tanino; Kosuke Namba
  Communications Chemistry, 3, 1, Springer Science and Business Media LLC, 09 Jan. 2020
  Scientific journal, Abstract
  
  For the fluorescence imaging of biologically active small compounds, the development of compact fluorophores that do not perturb bioactivity is required. Here we report a compact derivative of fluorescent 1,3a,6a-triazapentalenes, 2-isobutenylcarbonyl-1,3a,6a-triazapentalene (TAP-VK1), as a fluorescent labeling reagent. The reaction of TAP-VK1 with various aliphatic thiols proceeds smoothly to afford the corresponding 1,4-adducts in high yields, and nucleophiles other than thiols do not react. After the addition of thiol groups in dichloromethane, the emission maximum of TAP-VK1 shifts to a shorter wavelength and the fluorescence intensity is substantially increased. The utility of TAP-VK1 as a compact fluorescent labeling reagent is clearly demonstrated by the labeling of Captopril, which is a small molecular drug for hypertension. The successful imaging of Captopril, one of the most compact drugs, in this study demonstrates the usefulness of compact fluorophores for mechanistic studies.
• Studies on the 2^nd Generation Symthesis of Palau’amine
  Ohashi Eisaku; Takeuchi Kohei; Nakayama Atsushi; Karanjit S.; Tanino Keiji; Namba Kosuke
  Symposium on the Chemistry of Natural Products, symposium papers, 62, 7-12, Symposium on the Chemistry of Natural Products Steering Committee, 2020
  Japanese
• Synthetic study of andrastins: stereoselective construction of the BCD-ring system
  Fumihiko Yoshimura; Taiki Abe; Yuichi Ishioka; Keiji Tanino
  The Journal of Antibiotics, 72, 6, 384, 388, Springer Science and Business Media LLC, Jun. 2019, [Peer-reviewed], [Invited], [Last author, Corresponding author]
  Scientific journal
• Inhibition of lipid droplet formation by Ser/Thr protein phosphatase PPM1D inhibitor, SL-176
  Rui Kamada; Nozomi Kimura; Fumihiko Yoshimura; Keiji Tanino; Kazuyasu Sakaguchi
  PLOS ONE, 14, 2, e0212682, e0212682, Public Library of Science (PLoS), 27 Feb. 2019, [Peer-reviewed]
  Scientific journal
• Synthesis of Substituted Cyclopentenol Derivatives via Intramolecular Addition Reaction of Vinylcopper Species
  Yamaga, Hideomi; Tanino, Keiji
  Synlett, 30, 2, 230, 234, 2019, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Asymmetric Total Synthesis of Laurallene
  Yoshimura, Fumihiko; Okada, Taku; Tanino, Keiji
  Organic Letters, 21, 2, 559, 562, Jan. 2019, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• An Intermolecular [4+3] Cycloaddition Reaction Using 3-Hydroxy-2-pyrone Derivatives with an Oxyallyl Cation
  Takahiro Suzuki; Keiji Tanino; Takamune Yanagisawa
  HETEROCYCLES, 99, 2, 848, 848, The Japan Institute of Heterocyclic Chemistry, 2019, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Asymmetric Total Synthesis of Brasilicardins
  Fumihiko Yoshimura; Ryusei Itoh; Makoto Torizuka; Genki Mori; Keiji Tanino
  Angewandte Chemie, 130, 52, 17407, 17413, Wiley, 21 Dec. 2018
  Scientific journal
• Asymmetric Total Synthesis of Brasilicardins
  Fumihiko Yoshimura; Ryusei Itoh; Makoto Torizuka; Genki Mori; Keiji Tanino
  Angewandte Chemie International Edition, 57, 52, 17161, 17167, Wiley, Dec. 2018, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Asymmetric Total Synthesis of (-)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family
  Suzuki; Takahiro; Watanabe, Soichiro; Uyanik, Muhamme; Ishihara, Kazuaki; Kobayashi; Susumu; Tanino, Keiji
  Organic Letters, 20, 13, 3919, 3922, Jul. 2018, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ
  Fumihiko Yoshimura; Hiroki Saito; Taiki Abe; Keiji Tanino
  SYNLETT, 28, 14, 1816, 1820, Sep. 2017, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Inhibition of Ser/Thr phosphatase PPM1D induces neutrophil differentiation in HL-60 cells
  Rui Kamada; Fuki Kudoh; Fumihiko Yoshimura; Keiji Tanino; Kazuyasu Sakaguchi
  The Journal of Biochemistry, 09 May 2017, [Peer-reviewed]
  Scientific journal
• Non-reductive decyanation reactions of disubstituted malononitrile derivatives promoted by NaHMDS
  Daisuke Domon; Masaru Iwakura; Keiji Tanino
  TETRAHEDRON LETTERS, 58, 20, 1957, 1960, May 2017, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Synthetic studies on psiguadial B: Construction of bicyclo[4.3.1]decane skeleton via double cyclization reaction of alkyne dicobalt complex
  Masahiko Kinebuchi; Ryohei Uematsu; Keiji Tanino
  TETRAHEDRON LETTERS, 58, 14, 1382, 1386, Apr. 2017, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Construction of bicyclic systems containing an oxygen bridge by isomerization of cyclic epoxy alcohols
  Masaru Iwakura; Hiroshi Tokura; Keiji Tanino
  TETRAHEDRON LETTERS, 58, 12, 1223, 1226, Mar. 2017, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin
  Takahiro Suzuki; Soichiro Watanabe; Susumu Kobayashi; Keiji Tanino
  ORGANIC LETTERS, 19, 4, 922, 925, Feb. 2017, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Total Synthesis of Palau’amine
  Kosuke Namba; Kohei Takeuchi; Yukari Kaihara; Keiji Tanino
  Journal of Synthetic Organic Chemistry, Japan, 75, 11, 1094, 1101, The Society of Synthetic Organic Chemistry, Japan, 2017, [Peer-reviewed], [Invited], [Last author]
  English, Scientific journal
• Functional 1,3a,6a-triazapentalene scaffold: Design of fluorescent probes for kinesin spindle protein (KSP)
  Jun-ichi Sawada; Ayumi Osawa; Tomoki Takeuchi; Masato Kaneda; Shinya Oishi; Nobutaka Fujii; Akira Asai; Keiji Tanino; Kosuke Namba
  Bioorganic & Medicinal Chemistry Letters, 26, 23, 5765, 5769, Dec. 2016, [Peer-reviewed], [International Magazine]
  English, Scientific journal
• Synthetic studies on enfumafungin: stereoselective synthesis of the CD ring segment
  Manabu Fujitani; Keiji Tanino
  TETRAHEDRON LETTERS, 57, 43, 4838, 4841, Oct. 2016, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Effective Cellular Morphology Analysis for Differentiation Processes by a Fluorescent 1,3a,6a-Triazapentalene Derivative Probe in Live Cells
  Rui Kamada; Fumi Tano; Fuki Kudoh; Nozomi Kimura; Yoshiro Chuman; Ayumi Osawa; Kosuke Namba; Keiji Tanino; Kazuyasu Sakaguchi
  PLOS ONE, 11, 8, e0160625, e0160625, 04 Aug. 2016, [Peer-reviewed]
  English, Scientific journal
• Facile Guanidine Formation under Mild Acidic Conditions
  Takeuchi, Kohei; Nakayama, Atsushi; Tanino, Keiji; Namba, Kosuke
  Synlett, 27, 18, 2591, 2596, 01 Aug. 2016, [Peer-reviewed], [Last author]
  Scientific journal
• Synthesis of Aryl Amine Derivatives from Benzyl Nitriles via Electrocyclization of in Situ Generated N-SiIyl Ketene Imines
  Fumihiko Yoshimura; Taiki Abe; Keiji Tanino
  ORGANIC LETTERS, 18, 7, 1630, 1633, Apr. 2016, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Substituent Effect at the C4-Position of 1,3a,6a-Triazapentalene
  Atsushi Nakayama; Satoshi Nishio; Akira Otani; Akane Mera; Ayumi Osawa; Keiji Tanino; Kosuke Namba
  Chemical and Pharmaceutical Bulletin, 64, 7, 830, 837, 2016, [Peer-reviewed]
  English, Scientific journal
• Total synthesis of palau'amine
  Kosuke Namba; Kohei Takeuchi; Yukari Kaihara; Masataka Oda; Akira Nakayama; Atsushi Nakayama; Masahiro Yoshida; Keiji Tanino
  NATURE COMMUNICATIONS, 6, 8731, Nov. 2015, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Novel inhibitors targeting PPM1D phosphatase potently suppress cancer cell proliferation
  Ogasawara, Sari; Kiyota, Yuhei; Chuman, Yoshiro; Kowata, Ayano; Yoshimura, Fumihiko; Tanino, Keiji; Kamada, Rui; Sakaguchi, Kazuyasu
  Bioorganic & Medicinal Chemistry, 23, 19, 6246, 6249, Oct. 2015, [Peer-reviewed]
  Scientific journal
• Acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles
  Shibata, Miki; Fuchigami, Ryuichi; Kotaka, Ryota; Namba, Kosuke; Tanino, Keiji
  Tetrahedron, 71, 26-27, 4495, 4499, Jul. 2015, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Synthesis of yellow and red fluorescent 1,3a, 6a-triazapentalenes and the theoretical investigation of their optical properties
  Namba, Kosuke; Osawa, Ayumi; Nakayama, Akira; Mera, Akane; Tano, Fumi; Chuman, Yoshiro; Sakuda, Eri; Taketsugu, Tetsuya; Sakaguchi, Kazuyasu; Kitamura; Noboru; Tanino, Keiji
  Chemical Science, 6, 2, 1083, 1093, 2015, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Synthetic studies on azadirachtin: construction of the ABC ring system via the Diels-Alder reaction of a vinyl allenylsilane derivative
  Sakurai, Kentaro; Tanino, Keiji
  Tetrahedron Letters, 56, 3, 496, 499, Jan. 2015, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Inhibition of C-terminal truncated PPM1D enhances the effect of doxorubicin on cell viability in human colorectal carcinoma cell line
  Kozakai, Yuuki; Kamada, Rui; Kiyota, Yuhei; Yoshimura, Fumihiko; Tanino, Keiji; Sakaguchi, Kazuyasu
  Bioorganic & Medicinal Chemistry Letters, 24, 24, 5593, 5596, Dec. 2014, [Peer-reviewed]
  Scientific journal
• N-Acyl-N-tosylhydrazine as a Synthon To Construct Tetrasubstituted Carbon Centers Possessing a Nitrogen Group
  Namba, Kosuke; Shobo, Yoshihiro; Fujimoto, Kazuki; Shoji, Isamu; Yoshida, Masahiro; Tanino, Keiji
  European Journal of Organic Chemistry, 2014, 24, 5196, 5203, Aug. 2014, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions
  Fumihiko Yoshimura; Taiki Abe; Keiji Tanino
  Synlett, 25, 13, 1863, 1868, 24 Jun. 2014, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Cyanoazulene-based Multistage Redox Systems Prepared from Vinylcyclopropanecarbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach
  Keiji Tanino; Takumasa Yamada; Fumihiko Yoshimura; Takanori Suzuki
  Chemistry Letters, 43, 5, 607, 609, 05 May 2014, [Peer-reviewed], [Lead author, Corresponding author]
  English, Scientific journal
• Recent developments in the synthesis of zoanthamine alkaloids
  Fumihiko Yoshimura; Keiji Tanino; Masaaki Miyashita
  Tetrahedron Letters, 55, 18, 2895, 2903, Apr. 2014, [Peer-reviewed], [Invited]
  English, Scientific journal
• Synthesis of 1-acetyl-2-silyoxycycloheptane derivatives via highly stereoselective formal [5+2] cycloaddition reaction
  Kudo, Mami; Kondo, Fumikatsu; Maekawa, Hideki; Shimizu, Tadashi; Miyashita, Masaaki; Tanino, Keiji
  Tetrahedron Letters, 55, 6, 1192, 1195, Feb. 2014, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Stereoselective synthesis of the right-hand segment of tubiferal A
  Hiramatsu, Takahiro; Takahashi, Motomasa; Tanino, Keiji
  Tetrahedron Letters, 55, 6, 1145, 1147, Feb. 2014, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Synthetic studies on taxanes: construction of the tricyclic skeleton on the basis of a [6+2] cycloaddition reaction
  Ryosuke Hanada; Katsuhiko Mitachi; Keiji Tanino
  TETRAHEDRON LETTERS, 55, 5, 1097, 1099, Jan. 2014, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Synthesis of 2-cyano-1,4-cycloheptadiene derivatives via divinylcyclopropane rearrangement and alkylation of novel cycloheptadienyl anion species
  Yamada, Takumasa; Yoshimura, Fumihiko; Tanino, Keiji
  Tetrahedron Letters, 54, 6, 522, 525, Feb. 2013, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• SYNTHESIS OF TETRASUBSTITUTED PYRROLIDINE DERIVATIVES EMPLOYING beta-LACTAM AS A CHIRAL BUILDING BLOCK
  Tadano, Genta; Ishikura, Koji; Tanino, Keiji
  Heterocycles, 87, 11, 2267, 2267, 2013, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Chemical synthesis of zoanthamine alkaloids
  Fumihiko Yoshimura; Keiji Tanino; Masaaki Miyashita
  Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 71, 2, 124, 135, 2013, [Peer-reviewed], [Invited]
  Japanese
• Transformations of 1-(Oxiranylmethyl)-1,2,3-triazoles into 2-(Oxiranyl­methyl)-1,2,3-triazoles and Alkanenitriles
  Ayumi Osawa; Akane Mera; Kosuke Namba; Keiji Tanino
  Synlett, 24, 02, 207, 210, Georg Thieme Verlag KG, 19 Dec. 2012, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• One-Pot Synthesis of Highly Fluorescent 2,5-Disubstituted-1,3a,6a-triazapentalene
  Kosuke Namba; Akane Mera; Ayumi Osawa; Eri Sakuda; Noboru Kitamura; Keiji Tanino
  Organic Letters, 14, 21, 5554, 5557, 02 Nov. 2012, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Concise [4+3] cycloaddition reaction of pyrroles leading to tropinone derivatives
  Ryuichi Fuchigami; Kosuke Namba; Keiji Tanino
  Tetrahedron Letters, 53, 43, 5725, 5728, Oct. 2012, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• 38 Organic Chemistry Research on Iron Acquisition in Graminaceous Plants(Oral Presentation)
  Namba Kosuke; Murata Yoshiko; Kobayashi Kaori; Kanaki Michika; Osawa Ayumi; Nishizawa Mugio; Kusumoto Shoichi; Tanino Keiji
  Symposium on the Chemistry of Natural Products, symposium papers, 54, 223, 228, Symposium on the chemistry of natural products, 01 Sep. 2012
  Japanese, Symposium, Crops grown on alkaline soils, which cover about one-third of the world lands, are prone to iron-deficiency stress because of the low solubility of iron there. To acquire the insoluble iron efficiently, graminaceous plants have developed a unique strategy characterized by the synthesis and secretion of an iron-chelator phytosiderophore and a specific uptake system of iron(III) in its complex. Mugineic acid (MA) 1 was first identified as phytosiderophore in barley and its analogues have then been isolated and identified from various graminaceous species and cultivars; they all form water-soluble 1:1 complexes with iron(III). Owing to its significant implication in plant physiology, this iron up-take system has been a subject of intensive research since its discovery 30 years ago. However, a limited supply of phytosiderophores has been a severe bottleneck particularly for the study on the transport mechanism. Therefore, it is essential to establish an ample supply source of MA 1 and/or 2'-deoxymugineic acid (DMA) 2. In addition, supply of DMA will be potentially important to solve the worldwide problem of shortage of food supply because their use may make cultivation possible even on alkaline soils which are not favorable for farming. In this presentation, 1) the investigation of potential values of DMA as a fertilizer and synthetic studies toward an ample supply of DMA, 2) the mugineic acid derivatives as molecular probes for the mechanistic elucidation, and 3) development of 1,3a,6a-triazapentalenes as a breakthrough fluorescent molecule will be discussed. 1) A practical synthesis of L-azetidine-2-carboxylic acid, an expensive starting material for DMA, was established by using asymmetric organocatalyst. The normal rice plant was able to grow even in alkaline hydroponic culture by the addition of DMA and iron(III) salt. 2) A hydroxy group in mugineic acid (MA) that was not needed for Fe(III) complexation was used for the introduction of various labeling groups through propargylation and a click reaction. Labeled MA was incorporated as a phytosiderophore into Xenopus oocytes through the HvYS1 transporter, as determined by an electrophysiological assay and fluorescence microscopy. 3) An efficient and versatile method was established for the preparation of 1,3a,6a-triazapentalenes. The 1,3a,6a-triazapentalene skeleton without an additional fused ring system was discovered to be a compact and highly fluorescent chromophore, which exhibited various interesting fluorescent properties such as a noteworthy correlation of luminescent wavelength with the Hammett σ_p value and a strongly positive solvatofluorochromism.
• Total Synthesis of Zoanthamine Alkaloids
  Yoshimura, Fumihiko; Tanino, Keiji; Miyashita, Masaaki
  Accounts of Chemical Research, 45, 5, 746, 755, 15 May 2012, [Peer-reviewed], [Invited]
  Scientific journal
• Hg(OTf)(2)-Catalyzed Vinylogous Semi-Pinacol Rearrangement Leading to 1,4-Dihydroquinolines
  Namba, Kosuke; Kanaki, Michika; Suto, Hiroki; Nishizawa, Mugio; Tanino, Keiji
  Organic Letters, 14, 5, 1222, 1225, 02 Mar. 2012, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms
  Fumihiko Yoshimura; Keiji Tanino; Makoto Torizuka; Genki Mori
  Synlett, 2012, 02, 251, 254, Jan. 2012, [Peer-reviewed], [Corresponding author]
  English, Scientific journal
• A small molecule inhibitor of p53-inducible protein phosphatase PPM1D
  Yagi, Hiroaki; Chuman, Yoshiro; Kozakai, Yuuki; Imagawa; Toshiaki; Takahashi, Yu; Yoshimura, Fumihiko; Tanino, Keiji; Sakaguchi, Kazuyasu
  Bioorganic & Medicinal Chemistry Letters, 22, 1, 729, 732, Jan. 2012, [Peer-reviewed]
  Scientific journal
• Stereocontrolled synthesis of carbocyclic compounds with a quaternary carbon atom based on SN2′ alkylation of γ,δ-epoxy-α,β-unsaturated ketones
  Fumihiko Yoshimura; Ayano Kowata; Keiji Tanino
  Organic & Biomolecular Chemistry, 10, 28, 5431, 5431, 2012, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Direct Synthesis of Fluorescent 1,3a,6a-Triazapentalene Derivatives via Click-Cyclization-Aromatization Cascade Reaction
  Namba, Kosuke; Osawa, Ayumi; Ishizaka, Shoji; Kitamura; Noboru; Tanino, Keiji
  Journal of the American Chemical Society, 133, 30, 11466, 11469, 03 Aug. 2011, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Total synthesis of solanoeclepin A
  Tanino, Keiji; Takahashi, Motomasa; Tomata, Yoshihide; Tokura, Hiroshi; Uehara, Taketo; Narabu, Takashi; Miyashita, Masaaki
  Nature Chemistry, 3, 6, 484, 488, Jun. 2011, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Synthetic Studies of the Zoanthamine Alkaloids: Total Synthesis of Zoanthenol Based on an Isoaromatization Strategy
  Yoshimura, Fumihiko; Takahashi, Yu; Tanino, Keiji; Miyashita, Masaaki
  Chemistry-an Asian Journal, 6, 3, 922, 931, 01 Mar. 2011, [Peer-reviewed], [Corresponding author]
  Scientific journal
• Formal [6+4] cycloaddition of a dicobalt acetylene complex with furan derivatives
  Dota, Koichiro; Shimizu, Tadashi; Hasegawa, Shoji; Miyashita, Masaaki; Tanino, Keiji
  Tetrahedron Letters, 52, 8, 910, 912, Feb. 2011, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Mugineic Acid Derivatives as Molecular Probes for the Mechanistic Elucidation of Iron Acquisition in Barley
  Namba, Kosuke; Kobayashi; Kaori; Murata, Yoshiko; Hirakawa, Hiroko; Yamagaki, Tohru; Iwashita, Takashi; Nishizawa, Mugio; Kusumoto, Shoichi; Tanino, Keiji
  Angewandte Chemie-International Edition, 49, 51, 9956, 9959, 17 Dec. 2010, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Asymmetric Total Synthesis of Glycinoeclepin A: Generation of a Novel Bridgehead Anion Species
  Yasuhiro Shiina; Yoshihide Tomata; Masaaki Miyashita; Keiji Tanino
  Chemistry Letters, 39, 8, 835, 837, 05 Aug. 2010, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity
  Fukuda, Koichiro; Miyashita, Masaaki; Tanino, Keiji
  Tetrahedron Letters, 51, 34, 4523, 4525, Aug. 2010, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Cyclooctanone synthesis via a formal [6+2] cycloaddition reaction of a dicobalt acetylene complex
  Mitachi, Katsuhiko; Shimizu, Tadashi; Miyashita, Masaaki; Tanino, Keiji
  Tetrahedron Letters, 51, 30, 3983, 3986, Jul. 2010, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Total Synthesis of Furanether B. Construction of a Hydroazulene Skeleton via a Novel [5 + 2] Cycloaddition Reaction of Silyloxyallene
  Katsuhiko Mitachi; Takashi Yamamoto; Fumikatsu Kondo; Tadashi Shimizu; Masaaki Miyashita; Keiji Tanino
  Chemistry Letters, 39, 6, 630, 632, 05 Jun. 2010, [Peer-reviewed], [Last author, Corresponding author]
  English, Scientific journal
• Synthetic studies on azadirachtin: stereoselective construction of the ABCE ring system
  Nakagawa, Daisuke; Miyashita, Masaaki; Tanino, Keiji
  Tetrahedron Letters, 51, 20, 2771, 2773, May 2010, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Total Synthesis of Zoanthenol
  Takahashi, Yu; Yoshimutra, Fumihiko; Tanino, Keiji; Miyashita, Masaaki
  Angewandte Chemie-International Edition, 48, 47, 8905, 8908, 09 Nov. 2009, [Peer-reviewed], [Corresponding author]
  Scientific journal
• 4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide
  Namba, Kosuke; Shoji, Isamu; Nishizawa, Mugio; Tanino, Keiji
  Organic Letters, 11, 21, 4970, 4973, 05 Nov. 2009, [Peer-reviewed], [Last author, Corresponding author]
  Scientific journal
• Stereoselective S(N)2 ' alkylation reaction sequence of the gamma,delta-epoxy alpha,beta-unsaturated ester system via gamma,delta-chlorohydrin intermediates by the use of a R3Al-CuCN reagent
  Yoshimura, Fumihiko; Matsui, Atsushi; Hirai, Atsushi; Tanino, Keiji; Miyashita, Masaaki
  Tetrahedron Letters, 50, 36, 5126, 5129, Sep. 2009, [Peer-reviewed], [Corresponding author]
  Scientific journal
• Toward Palau'amine: Hg(OTf)(2)-Catalyzed Synthesis of the Cyclopentane Core
  Namba, Kosuke; Kaihara, Yukari; Yamamoto; Hirofumi; Imagawa, Hiroshi; Tanino, Keiji; Williams; Robert M.; Nishizawa, Mugio
  Chemistry-a European Journal, 15, 27, 6560, 6563, 06 Jul. 2009, [Peer-reviewed]
  Scientific journal
• Synthetic Studies of the Zoanthamine Alkaloids: The Total Syntheses of Norzoanthamine and Zoanthamine
  Yoshimura, Fumihiko; Sasaki, Minoru; Hattori, Izumi; Komatsu, Kei; Sakai, Mio; Tanino, Keiji; Miyashita, Masaaki
  Chemistry-a European Journal, 15, 27, 6626, 6644, 06 Jul. 2009, [Peer-reviewed]
  Scientific journal
• An Efficient Synthetic Method for 3-Bromofuran Derivatives via Stereoselective Cyclization of γ,δ-Epoxy-(E)-α-bromoacrylates
  Masaaki Miyashita; Fumihiko Yoshimura; Masaki Takahashi; Keiji Tanino
  HETEROCYCLES, 77, 1, 201, 201, 2009, [Peer-reviewed]
  English, Scientific journal
• Stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems
  Yu, Xiao-Qiang; Yoshimura, Fumihiko; Tanino, Keiji; Miyashita, Masaaki
  Tetrahedron Letters, 49, 52, 7442, 7445, Dec. 2008, [Peer-reviewed]
  Scientific journal
• Stereospecific epoxide-opening reactions of 1,1-dibromo-3,4-epoxy-1-alkenes with carbon nucleophiles
  Yoshimura, Fumihiko; Takahashi, Masaki; Tanino, Keiji; Miyashita, Masaaki
  Tetrahedron Letters, 49, 49, 6991, 6994, Dec. 2008, [Peer-reviewed]
  Scientific journal
• Palladium-catalyzed stereospecific substitution of alpha,beta-unsaturated gamma,delta-epoxy esters by alcohols with double inversion of configuration: Synthesis of 4-alkoxy-5-hydroxy-2-pentenoates
  Yu, Xiao-Qiang; Yoshimura, Fumihiko; Ito, Fumito; Sasaki, Minoru; Hirai, Atsushi; Tanino, Keiji; Miyashita, Masaaki
  Angewandte Chemie-International Edition, 47, 4, 750, 754, 11 Jan. 2008, [Peer-reviewed]
  Scientific journal
• Synthesis of alicyclic esters via an intramolecular conjugate addition reaction. New method for generating (Z)-vinylcopper species from 1,1-dibromoalkenes
  Tanino, K.; Arakawa, K.; Satoh, M.; Iwata, Y.; Miyashita, M.
  Tetrahedron Letters, 47, 6, 861, 864, Feb. 2006, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• A novel cyclopentene annulation method based on conjugate addition reactions of alpha-cyano carbanion species
  Tanino, K.; Tomata, Y.; Shiina, Y.; Miyashita, M.
  European Journal of Organic Chemistry, 2006, 2, 328, 334, Jan. 2006, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Total synthesis of ingenol
  Kuwajima, I; K Tanino
  CHEMICAL REVIEWS, 105, 12, 4661, 4670, Dec. 2005, [Peer-reviewed], [Invited], [Last author]
  English
• Pd-Catalyzed Stereospecific Azide Substitution of α,β-Unsaturated γ,δ-Epoxy Esters with Double Inversion of Configuration
  Masaaki Miyashita; Taiku Mizutani; Genta Tadano; Yasuhiro Iwata; Masahiro Miyazawa; Keiji Tanino
  Angewandte Chemie International Edition, 44, 32, 5094, 5097, 12 Aug. 2005, [Peer-reviewed], [Last author]
  Scientific journal
• Stereoselective synthesis of premisakinolide A, the monomeric counterpart of the marine 40-membered dimeric macrolide misakinolide A
  Nakamura, R.; Tanino, K.; Miyashita, M.
  Organic Letters, 7, 14, 2929, 2932, 01 Jul. 2005, [Peer-reviewed]
  Scientific journal
• Synthetic studies of tedanolide, a marine macrolide displaying potent antitumor activity. Stereoselective synthesis of the C(13)-C(23) segment
  Iwata, Y.; Tanino, K.; Miyashita, M.
  Organic Letters, 7, 12, 2341, 2344, Jun. 2005, [Peer-reviewed]
  Scientific journal
• Tetramic acid antibiotics: Stereoselective synthesis of streptolic acid and tirandalydigin
  Iwata, Y.; Maekawara, N.; Tanino, K.; Miyashita, M.
  Angewandte Chemie-International Edition, 44, 10, 1532, 1536, 25 Feb. 2005, [Peer-reviewed]
  Scientific journal
• Synthesis of cyclobutanones and four-membered enol ethers by using a rearrangement reaction of enol triflates
  Tanino, K.; Aoyagi, K.; Kirihara, Y.; Ito, Y.; Miyashita, M.
  Tetrahedron Letters, 46, 7, 1169, 1172, Feb. 2005, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Natural product synthesis based on new acyclic stereocontrol. Stereoselective total syntheses of zincophorin, the lonophore antibiotic, and scytophycin, an antitumor marine macrolide
  M Miyashita; K Tanino
  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 62, 11, 1080, 1094, Nov. 2004, [Peer-reviewed], [Invited], [Last author]
  English, Scientific journal
• Stereoselective total synthesis of the ionophore antibiotic zincophorin
  Komatsu, K.; Tanino, K.; Miyashita, M.
  Angewandte Chemie-International Edition, 43, 33, 4341, 4345, 20 Aug. 2004, [Peer-reviewed]
  Scientific journal
• Total synthesis of norzoanthamine
  Miyashita, M.; Sasaki, M.; Hattori, I.; Sakai, M.; Tanino, K.
  Science, 305, 5683, 495, 499, 23 Jul. 2004, [Peer-reviewed]
  Scientific journal
• Regio- and stereospecific alkyl and alkynyl substitution reactions of epoxy selenides with organoaluminums via episelenonium ions
  Sasaki, M.; Hatta, M.; Tanino, K.; Miyashita, M.
  Tetrahedron Letters, 45, 9, 1911, 1913, Feb. 2004, [Peer-reviewed]
  Scientific journal
• The first C2 selective halide substitution reaction of 2,3-epoxy alcohols by the use of (CH3O)(3)B-MX (X=I, Br, Cl) system
  Tomata, Y.; Sasaki, M.; Tanino, K.; Miyashita, M.
  Tetrahedron Letters, 44, 50, 8975, 8977, Dec. 2003, [Peer-reviewed]
  Scientific journal
• Total synthesis of scytophycin C. 2. Coupling reaction of the C(1)-C(18) segment and the C(19)-C(31) segment, a key macrolactonization, and the crucial terminal amidation reaction
  Nakamura, R.; Tanino, K.; Miyashita, M.
  Organic Letters, 5, 20, 3583, 3586, 01 Oct. 2003, [Peer-reviewed]
  Scientific journal
• Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segment
  Nakamura, R.; Tanino, K.; Miyashita, M.
  Organic Letters, 5, 20, 3579, 3582, 01 Oct. 2003, [Peer-reviewed]
  Scientific journal
• The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: The first endo-mode epoxide-opening reaction through an intramolecular metal chelate
  Sasaki, M.; Tanino, K.; Hirai, A.; Miyashita, M.
  Organic Letters, 5, 10, 1789, 1791, 01 May 2003, [Peer-reviewed]
  Scientific journal
• Total Synthesis of Ingenol
  Keiji Tanino; Kei Onuki; Kohei Asano; Masaaki Miyashita; Tsuyoshi Nakamura; Yoshinori Takahashi; Isao Kuwajima
  Journal of the American Chemical Society, 125, 6, 1498, 1500, 01 Feb. 2003, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Stereospecific synthesis of aldoses based on the epoxide-opening reaction with double inversion of the configuration
  Atsushi Hirai; Terumichi Tonooka; Keiji Tanino; Masaaki Miyashita
  Chirality, 15, 1, 108, 109, 2003, [Peer-reviewed]
  English, Scientific journal
• Stereoselective synthesis of cycloheptanone derivatives via an intermolecular [5+2] cycloaddition reaction
  Tanino, K.; Kondo, F.; Shimizu, T.; Miyashita, M.
  Organic Letters, 4, 13, 2217, 2219, 01 Jun. 2002, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Stereospecific interconversion between cis and trans 2,3-epoxysulfides
  Hirai, A.; Tonooka, T.; Wakatsuki, K.; Tanino, K.; Miyashita, M.
  Angewandte Chemie-International Edition, 41, 5, 819, 821, 01 Mar. 2002, [Peer-reviewed]
  Scientific journal
• Synthetic studies of zoanthamine alkaloids. Stereoselective synthesis of the ABC ring system of norzoanthamine by an intramolecular Diels-Alder reaction
  Sakai, M.; Sasaki, M.; Tanino, K.; Miyashita, M.
  Tetrahedron Letters, 43, 9, 1705, 1708, Feb. 2002, [Peer-reviewed]
  Scientific journal
• A regio- and stereoselective alpha-methylation of gamma,delta-epoxy-alpha,beta-unsaturated esters with a Me2Zn-CuCN reagent
  Hirai, A.; Matsui, A.; Komatsu, K.; Tanino, K.; Miyashita, M.
  Chemical Communications, 17, 1970, 1971, 2002, [Peer-reviewed]
  Scientific journal
• Stereospecific alkyl and alkynyl substitution reactions of epoxy sulfides with organoaluminums with double inversion of the configuration
  Sasaki, M.; Tanino, K.; Miyashita, M.
  Journal of Organic Chemistry, 66, 16, 5388, 5394, 01 Aug. 2001, [Peer-reviewed]
  Scientific journal
• Development of new reactions for carbon-carbon bond formation by using carbocation species
  K Tanino
  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 59, 6, 549, 559, Jun. 2001, [Peer-reviewed], [Invited], [Corresponding author]
  Japanese
• Regioselective alkyl and alkynyl substitution reactions of epoxy alcohols by the use of organoaluminum ate complexes: Regiochemical reversal of nucleophilic substitution reactions
  Sasaki, M.; Tanino, K.; Miyashita, M.
  Organic Letters, 3, 11, 1765, 1767, May 2001, [Peer-reviewed]
  Scientific journal
• Synthesis of cyclic allenylsilanes via an intramolecular substitution reaction of 1-siloxy-2,3-epoxyalkanes
  Tanino, K.; Honda, Y.; Miyashita, M.
  Tetrahedron Letters, 41, 48, 9281, 9285, Nov. 2000, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• An intramolecular hetero Diels-Alder reaction of alpha-(alkynylsiloxy)aldimine derivatives
  Shimizu, T.; Tanino, K.; Kuwajima, I.
  Tetrahedron Letters, 41, 30, 5715, 5718, Jul. 2000, [Peer-reviewed], [Corresponding author]
  Scientific journal
• A novel [5+2] cycloaddition reaction using a dicobalt acetylene complex
  Tanino, K.; Shimizu, T.; Miyama, M.; Kuwajima, I.
  Journal of the American Chemical Society, 122, 25, 6116, 6117, 01 Jun. 2000, [Peer-reviewed], [Lead author, Corresponding author]
  Scientific journal
• Regiocontrolled ring opening reactions of a cyclic acetal
  Egami, Y.; Takayanagi, M.; Tanino, K.; Kuwajima, I.
  Heterocycles, 52, 2, 583, 583, 2000, [Peer-reviewed], [Corresponding author]
  Scientific journal
• Stereoselective alkynylation of trans-2,3-epoxy sulfides with double inversion of configuration by alkynylaluminums
  Sasaki, M.; Miyazawa, M.; Tanino, K.; Miyashita, M.
  Tetrahedron Letters, 40, 52, 9267, 9270, Dec. 1999, [Peer-reviewed]
  Scientific journal
• A convenient method for the synthesis of Delta(1,6)-bicyclo[4.n.0]alken-2-ones
  Watanabe, N.; Tanino, K.; Kuwajima, I.
  Tetrahedron Letters, 40, 46, 8133, 8136, Nov. 1999, [Peer-reviewed], [Corresponding author]
  Scientific journal
• A new method for the synthesis of medium- and large-sized carbocycles
  Masuya, K.; Tanino, K.; Kuwajima, I.
  Synlett, 1999, 5, 647, 649, May 1999, [Peer-reviewed]
  Scientific journal
• Total synthesis of (-)-coriolin
  Mizuno, H.; Domon, K.; Masuya, K.; Tanino, K.; Kuwajima, I.
  Journal of Organic Chemistry, 64, 8, 2648, 2656, 01 Apr. 1999, [Peer-reviewed], [Corresponding author]
  Scientific journal
• A novel method for inside selective silylation of 1,2-diols
  Tanino, K.; Shimizu, T.; Kuwahara, M.; Kuwajima, I.
  Journal of Organic Chemistry, 63, 8, 2422, 2423, 01 Apr. 1998, [Peer-reviewed], [Lead author]
  Scientific journal
• Highly regio- and stereoselective [3+2] cyclopentanone annulation using a 3-(alkylthio)-2-siloxyallyl cationic species
  Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I.
  Journal of the American Chemical Society, 120, 8, 1724, 1731, 01 Mar. 1998, [Peer-reviewed]
  Scientific journal
• A new synthetic method for cyclic allenes and acetylenes. Cleavage of a C-C bond directed by a silyl group
  Sugai, M.; Tanino, K.; Kuwajima, I.
  Synlett, 1997, 5, 461, 462, Jun. 1997, [Peer-reviewed]
  Scientific journal
• Control of stereochemistry by sigma-participation of a silyl group. A novel method for diastereoselective polyol synthesis
  Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I.
  Journal of Organic Chemistry, 62, 13, 4206, 4207, 01 Jun. 1997, [Peer-reviewed], [Lead author]
  Scientific journal
• A new approach for ingenol synthesis
  Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I.
  Journal of Organic Chemistry, 62, 10, 3032, 3033, 01 May 1997, [Peer-reviewed], [Corresponding author]
  Scientific journal
• Highly efficient method for coriolin synthesis
  Domon, K.; Masuya, K.; Tanino, K.; Kuwajima, I.
  Tetrahedron Letters, 38, 3, 465, 468, Jan. 1997, [Peer-reviewed]
  Scientific journal
• Carbon-carbon bond formation using alkenylsulfides
  Keiji Tanino; Isao Kuwajima
  Phosphorus, Sulfur and Silicon and Related Elements, 120-121, 369, 370, Taylor and Francis Ltd., 1997, [Peer-reviewed], [Lead author]
  English, Scientific journal
• Methylenecyclopentane annulation via formal [3+2] cycloaddition reaction
  Takahashi, Y.; Tanino, K.; Kuwajima, I.
  Tetrahedron Letters, 37, 33, 5943, 5946, Aug. 1996, [Peer-reviewed]
  Scientific journal
• Diastereoselective introduction of carbon chain to pyrrolidone derivatives
  Sato, K.; Koga, T.; Masuya, K.; Tanino, K.; Kuwajima, I.
  Synlett, 1996, 8, 751, 751, Aug. 1996, [Peer-reviewed]
  Scientific journal
• A new synthetic method for cyclopentanones via formal [3+2] cycloaddition reaction
  Domon, KMK; Tanino, K.; Kuwajima, I.
  Synlett, 1996, 2, 157, 158, Feb. 1996, [Peer-reviewed]
  Scientific journal
• New aspects of vinylsulfide chemistry
  Isao Kuwajima; Keiji Tanino
  Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 54, 11, 929, 940, 1996, [Peer-reviewed], [Invited], [Last author]
  English, Scientific journal
• CONJUGATE ADDITION OF ALKENYLSULFIDES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - REMARKABLE N-PI(ASTERISK) ORBITAL INTERACTION FOR CONTROL OF REGIOCHEMISTRY AND STEREOCHEMISTRY
  TAKAYANAGI, M.; TANINO, K.; KUWAJIMA, I.
  Synlett, 1995, 2, 173, 174, Feb. 1995, [Peer-reviewed]
  Scientific journal
• 3-(ALKYLTHIO)-1,2-BIS(SILOXY)-3-BUTENES AS EFFICIENT CHIRALITY TRANSFERRED BUILDING-BLOCKS
  MASUYA, K.; TANINO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 35, 43, 7965, 7968, 10 Oct. 1994, [Peer-reviewed]
  Scientific journal
• HIGHLY STEREOSELECTIVE ENE REACTION OF ALDIMINES WITH 2-(ALKYLTHIO)ALLYL SILYL ETHERS
  TOHYAMA, Y.; TANINO, K.; KUWAJIMA, I.
  Journal of Organic Chemistry, 59, 3, 518, 519, Feb. 1994, [Peer-reviewed]
  Scientific journal
• A NOVEL TRANSFORMATION INVOLVING SELECTIVE FORMATION AND CLEAVAGE OF C-C BONDS
  TAKAYANAGI, M.; UMAMORI, N.; TANINO, K.; KUWAJIMA, I.
  Journal of the American Chemical Society, 115, 26, 12635, 12636, Dec. 1993, [Peer-reviewed]
  Scientific journal
• Construction of N-Acylated 4-Piperidones via Selective Carbon-Nitrogen and Carbon-Carbon Bond Formation
  Mitsumasa Takahashi; Keiji Tanino; Isao Kuwajima
  Chemistry Letters, 22, 10, 1655, 1658, Oct. 1993, [Peer-reviewed]
  English, Scientific journal
• LEWIS-ACID PROMOTED ENE-LIKE REACTIONS OF ENOL ETHERS WITH ALDEHYDES
  SHODA, H.; NAKAMURA, T.; TANINO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 34, 39, 6281, 6284, Sep. 1993, [Peer-reviewed]
  Scientific journal
• STRUCTURE OF AN OPTICALLY-ACTIVE ANTHRACYCLINE PRECURSOR
  KAMEI, S.; SAKAI, Y.; OHASHI, Y.; ADACHI, A.; TANINO, K.; KUWAJIMA, I.
  Acta Crystallographica Section C-Crystal Structure Communications, 49, 8, 1509, 1511, 15 Aug. 1993, [Peer-reviewed]
  Scientific journal
• AN ENANTIOSELECTIVE SYNTHESIS OF ANTHRACYCLINE PRECURSORS
  ADACHI, A.; MASUYA, K.; TANINO, K.; KUWAJIMA, I.
  Journal of Organic Chemistry, 58, 16, 4189, 4190, Jul. 1993, [Peer-reviewed]
  Scientific journal
• HIGHLY STEREOSELECTIVE CHELATION CONTROLLED ENE-REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHERS
  NAKAMURA, T.; TANINO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 34, 3, 477, 480, Jan. 1993, [Peer-reviewed]
  Scientific journal
• GENERATION OF A LEWIS ACID ACTIVATED FORMALDIMINE AND ITS REACTION WITH ENOL SILYL ETHERS - N-UNSUBSTITUTED AMINOMETHYLATION
  TANINO, K.; TAKAHASHI, M.; MURAYAMA, K.; KUWAJIMA, I.
  Journal of Organic Chemistry, 57, 26, 7009, 7010, Dec. 1992, [Peer-reviewed], [Lead author]
  Scientific journal
• Remarkable Stereochemical Features of Ene Reaction of 2-(Alkylthio)crotyl Silyl Ethers Proposal of a Six-Membered Chair-like Transition State
  Takashi Nakamura; Keiji Tanino; Isao Kuwajima
  Chemistry Letters, 21, 8, 1425, 1428, Aug. 1992, [Peer-reviewed]
  English, Scientific journal
• ENE REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHER INVOLVING A CHIRALITY TRANSFER
  TANINO, K.; SHODA, H.; NAKAMURA, T.; KUWAJIMA, I.
  Tetrahedron Letters, 33, 10, 1337, 1340, Mar. 1992, [Peer-reviewed], [Lead author]
  Scientific journal
• HIGHLY THREO-SELECTIVE ENE-REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHERS WITH ALDEHYDES
  TANINO, K.; NAKAMURA, T.; KUWAJIMA, I.
  Tetrahedron Letters, 31, 15, 2165, 2168, Jan. 1990, [Peer-reviewed], [Lead author]
  Scientific journal
• A SELECTIVE ONE-CARBON RING EXPANSION REACTION OF 1-SILOXYCYCLO-ALKANECARBALDEHYDES CATALYZED BY A LEWIS ACID
  MATSUDA, T.; TANINO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 30, 32, 4267, 4270, Jan. 1989, [Peer-reviewed]
  Scientific journal
• SILICON-BASED NUCLEOPHILE MEDIATED ONE-CARBON RING EXPANSION REACTION OF 1-(TRIMETHYLSILYLMETHYL)CYCLOALKANECARBALDEHYDES
  TANINO, K.; SATO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 30, 47, 6551, 6554, Jan. 1989, [Peer-reviewed], [Lead author]
  Scientific journal
• A HIGHLY SELECTIVE ONE-CARBON RING ENLARGEMENT REACTION DIRECTED BY SILICON
  TANINO, K.; KATOH, T.; KUWAJIMA, I.
  Tetrahedron Letters, 29, 15, 1819, 1822, Jan. 1988, [Peer-reviewed]
  Scientific journal
• A HIGHLY EFFICIENT METHOD FOR ONE-CARBON RING EXPANSION - PREPARATION OF 1-ALKOXY-2-METHYLENECYCLOALKANES
  KATOH, T.; TANINO, K.; KUWAJIMA, I.
  Tetrahedron Letters, 29, 15, 1815, 1818, Jan. 1988, [Peer-reviewed], [Lead author]
  Scientific journal
• Directing Effects of a Silyl Group on Cationic Rearrangement Reactions
  Keiji Tanino; Yasuo Hatanaka; Isao Kuwajima
  Chemistry Letters, 16, 2, 385, 388, 05 Feb. 1987, [Peer-reviewed], [Lead author]
  English, Scientific journal

• Molecular transformation of ketones to carboxylic acids via ring-opening reaction of epoxynitriles with a squarate anion
  藤田知之; 佐藤和都; 池内和忠; 谷野圭持, 日本化学会春季年会講演予稿集(Web), 105th, 2025
• ノルボルネン骨格含有三環性化合物の骨格転位によるブレンダン誘導体の合成
  吉谷明浩; 捧智成; 加藤蘭丸; 池内和忠; 谷野圭持, 有機合成シンポジウム講演予稿集, 124th, 2024
• Novel conversion method of cyclopentane-1,3-dione moiety: Construction of 5/5/4 tricyclic systems and its mechanistic studies
  小林誠; 捧智成; 谷野圭持; 中村精一; 池内和忠, 日本薬学会年会要旨集(Web), 144th, 2024
• Analysis of biosynthesis mechanism of hatching factors for potato cyst nematodes
  秋山遼太; 清水宏祐; 串田篤彦; 谷野圭持; 杉本幸裕; 水谷正治, 日本植物生理学会年会(Web), 65th, 2024
• Skeletal Rearrangement of Tricyclic Norbornene derivative with Bridgehead Hydroxyl groups
  吉谷明浩; 捧智成; 加藤蘭丸; 池内和忠; 谷野圭持, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 67th, 2023
• Identification of a novel hatching factor for potato cyst nematode, solanoeclepin B, and investigation of its biosynthesis
  秋山遼太; 清水宏祐; 坂田至; 串田篤彦; 渡辺文太; 谷野圭持; 杉本幸裕; 水谷正治, 日本植物生理学会年会(Web), 64th, 2023
• Biosynthesis and physiological roles of hatching factor for potato cyst nematodes
  秋山遼太; 清水宏祐; 坂田至; 串田篤彦; 谷野圭持; 杉本幸裕; 水谷正治, 植物の生長調節, 58, Supplement, 2023
• Structural analysis of substances related to potato cyst nematode hatching acceleration
  河野結; 秋山遼太; 清水宏祐; 坂田至; 串田篤彦; 谷野圭持; 杉本幸裕; 水谷正治, 植物の生長調節, 58, Supplement, 2023
• Synthesis of Tricyclo[4.2.1.0^3,7]nonane Derivatives Using Skeletal Rearrangement of Tricyclic Compounds Containing a Norbornene Substructure
  吉谷明浩; 捧智成; 加藤蘭丸; 池内和忠; 谷野圭持, 日本化学会春季年会講演予稿集(Web), 103rd, 2023
• Development of a method for the construction of a 7-norbornanone skeleton using 1,4-bis(silyloxy)-1,3-cyclopentadienes
  廣川歓人; 捧智成; 池内和忠; 谷野圭持, 日本化学会春季年会講演予稿集(Web), 103rd, 2023
• (+)-コリアミルチンの全合成
  池内和忠; 原口翔太; 藤井りょう; 山田英俊; 鈴木孝洋; 谷野圭持, 次世代を担う有機化学シンポジウム講演要旨集, 21st, 2023
• Analysis of synergy factor that enhances the activity of hatching factor for potato cyst nematode
  小川千景; 岡村勇哉; 清水宏祐; 坂田至; 串田篤彦; 谷野圭持; 杉本幸裕; 水谷正治, 日本農芸化学会大会講演要旨集(Web), 2022, 2022
• Identification of novel hatching factor for potato cyst nematode from potato hydroponic culture solution
  清水宏祐; 増田裕貴; 岡村勇哉; 小川千景; 秋山遼太; 渡辺文太; 坂田至; 串田篤彦; 谷野圭持; 杉本幸裕; 水谷正治, 日本農芸化学会大会講演要旨集(Web), 2022, 2022
• Exploration of a novel hatching factor for potato cyst nematode
  清水宏祐; 秋山遼太; 増田裕貴; 坂田至; 串田篤彦; 谷野圭持; 刑部敬史; 渡辺文太; 杉本幸裕; 水谷正治, 植物の生長調節, 57, Supplement, 2022
• Synthesis of 1,3-cyclopentadiones with an alkyl and a heteroaryl group at the C-2 position
  尾添祐介; 加藤蘭丸; 池内和忠; 谷野圭持, 日本化学会春季年会講演予稿集(Web), 102nd, 2022
• Synthesis of 1,3-cyclopentanediones bearing an alkyl group and a furan ring at the C-2 position via semi-pinacol rearrangement
  池内和忠; 尾添祐介; 加藤蘭丸; 谷野圭持, 日本薬学会年会要旨集(Web), 142nd, 2022
• Synthesis of norbornane compounds using the properties of 1,4-bissilyl enol ethers derived from 1,3-cyclopentanediones
  池内和忠; 池内和忠; 捧智成; 廣川歓人; 谷野圭持, メディシナルケミストリーシンポジウム講演要旨集, 39th (CD-ROM), 2022
• A Novel Synthetic Method for Bicyclo[2.2.2]octanes from Pyridazines Using An Intramolecular Diels-Alder Cascade
  今井隆史; 鈴木孝洋; 谷野圭持, 複素環化学討論会講演要旨集, 50th, 2021
• Improved synthetic study of atropurpuran
  古山岳史; 中西健太; 鈴木孝洋; 小林進; 谷野圭持, 日本化学会春季年会講演予稿集(CD-ROM), 100th, 2020
• Studies on the Second Generation Synthesis of Palau’ amine
  大橋栄作; 竹内公平; 竹内公平; 中山淳; KARANJIT Sangita; 谷野圭持; 難波康佑, 日本薬学会年会要旨集(Web), 140th, 2020
• ラジカル環化反応を利用したkamebaninの全合成
  池田航; 菅野彩夏; 鈴木孝洋; 谷野圭持, 有機合成シンポジウム講演予稿集, 116th, 2019
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 中山淳; KARANJIT Sangita; 谷野圭持; 難波康祐, 日本薬学会年会要旨集(CD-ROM), 139th, 2019
• Total Synthesis of Atropurpuran
  鈴木孝洋; 鈴木孝洋; 中西健太; 小林進; 谷野圭持, 天然有機化合物討論会講演要旨集(Web), 59th, 2017
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 竹内公平; 中山淳; 谷野圭持; 難波康祐, 創薬懇話会講演要旨集, 2017, 2017
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 竹内公平; 中山淳; 谷野圭持; 難波康祐, 日本薬学会年会要旨集(CD-ROM), 137th, 2017
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 竹内公平; 中山淳; 谷野圭持; 難波康祐, 有機合成シンポジウム講演要旨集, 111th, 2017
• ジャガイモシストセンチュウふ化促進物質の全合成 : シストセンチュウの根絶法を目指して (特集 自然界の神秘に挑む! 天然物の全合成) -- (全合成の最先端研究)
  谷野 圭持, 化学 = Chemistry, 71, 4, 52, 54, Apr. 2016
  化学同人, Japanese
• アイボレノイドAの全合成研究
  堀口耕作; 鈴木孝洋; 谷野圭持, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 60th, 2016
• 連続的環化反応を利用したent-カウレン類の合成研究
  菅野彩夏; 鈴木孝洋; 谷野圭持, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 60th, 2016
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 竹内公平; 中山淳; 谷野圭持; 難波康祐, 日本薬学会年会要旨集(CD-ROM), 136th, 2016
• Palau’amineの第二世代合成研究
  大橋栄作; 竹内公平; 竹内公平; 中山淳; 谷野圭持; 難波康祐, 創薬懇話会講演要旨集, 2016, 2016
• The PPM1D encoded phosphatase Wip1 is a novel oncogene and potential therapeutic target in neuroblastoma and medulloblastoma
  Jelena Miloseyic; Diana Treis; Malin Wickstrom; Susanne Fransson; Nina Eissler; Baldur Syeinbjornsson; Ninib Baryawno; Keiji Tanino; Galina Selivanova; Kazuyasu Sakaguchi; Tommy Martinsson; John Inge Johnsen; Per Kogner, CANCER RESEARCH, 75, Aug. 2015
  English, Summary international conference
• PREFACE TO HETEROCYCLES ISSUE HONORING THE 77TH BIRTHDAY OF PROFESSOR ISAO KUWAJIMA
  Keiji Tanino, HETEROCYCLES, 90, 1, 3, 5, Jan. 2015
  English, Others
• Total synthesis of solanoeclepin A, a key hatch-stimulating substance for the potato cyst nematode
  TANINO Keiji, 農林水産技術研究ジャーナル, 35, 5, 45, 48, 01 May 2012
  農林水産技術情報協会, Japanese
• Asymmetric Total Synthesis of Solanoeclepin A
  Takahashi Motomasa; Tomata Yoshihide; Tokura Hiroshi; Uehara Kento; Narabu Takashi; Miyashita Masaaki; Tanino Keiji, 天然有機化合物討論会講演要旨集, 52, 139, 144, 01 Sep. 2010
  Solanoeclepin A (1), isolated from a large quantity of potatoes as the most active hatching agent of potato cyst nematodes in 1986, possesses a unique heptacyclic structure containing all ring sizes from three to seven with various oxygen functional groups. The first asymmetric total synthesis of Solanoeclepin A was achieved on the basis of (1) the intramolucular Diels-Alder reaction of a 3-methoxyfuran derivative, and (2) an intramolecular cyclization reaction of an epoxy nitrile. Epoxy nitrile 6 was synthesized from optically active nitrile 7 through semi-pinacol rearrangement of epoxy alcohol 12 mediated by TMSOTf. Treatment of epoxy nitrile 6 with LDA followed by TBSCl and HMPA afforded the cyclization product 10 having a the tricyclo[5.2.1.0^<1.6>]decane skeleton in high yield. Elaboration of the cyclopropane side chain was effected by using the enantioselective cyclopropanation reaction reported by Charette. A methoxyfuran moiety and an enone side chain was introduced to the right-hand segment 22, and the product 26 was subjected to the crucial intramolecular Diels-Alder reaction promoted by Me_2AlCl. The product having the heptacyclic skeleton of Solanoeclepin A was obtained in 62% yield. Oxidation of the 7-membered ring and elaboration of other functional groups gave rise to synthetic Solanoeclepin A (total 52 steps, 0.11% overall yield)., Symposium on the chemistry of natural products, Japanese
• Identification of Novel Chemical Inhibitors for p53-Inducible Protein Phosphatase PPM1D
  YAGI Hiroaki; CHUMAN Yoshiro; YOSHIMURA Fumihiko; TANINO Keiji; SAKAGUCHI Kazuyasu, Peptide science : proceedings of the ... Japanese Peptide Symposium, 2008, 385, 386, 01 Mar. 2009
  English
• Structural Photomodulation of Peptides with Azobenzoate Derivative in Peptide Backbone
  KAMADA Rui; FUKUDA Kouichiro; MIYAZAKI Hiromitsu; NOMURA Takao; CHUMAN Yoshiro; IMAGAWA Toshiaki; TANINO Keiji; SAKAGUCHI Kazuyasu, Peptide science : proceedings of the ... Japanese Peptide Symposium, 2007, 447, 448, 01 Mar. 2008
  English
• グリシノエクレピンの不斉全合成研究 (第16回 天然薬物の開発と応用シンポジウム講演要旨集)
  椎名 康裕; 遠又 慶英; 谷野 圭持, 薬学雑誌, 126, 176, 179, 2006
  日本薬学会, Japanese
• 立体特異的鎖状有機分子構築法の開発と天然物合成への展開 (特集 天然物化学の技術進歩)
  宮下 正昭; 谷野 圭持, 化学工業, 55, 8, 583, 589, Aug. 2004
  化学工業社, Japanese

• 天然物全合成の最新動向
  シーエムシー出版, 2009
• 天然物化学 植物編
  アイピーシー, 2007
• 第５版実験化学講座 16有機化合物の合成IV
  丸善, 2005

• 総合化学特論Ⅱ(Modern Trends in Organic Chemistry and Biological Chemistry), 2024年, 修士課程, 総合化学院
• 大学院共通授業科目（一般科目）：自然科学・応用科学, 2024年, 修士課程, 大学院共通科目
• 総合化学特論II (Modern Trends in Organic Chemistry and Biological Chemistry), 2024年, 修士課程, 工学院
• 大学院共通授業科目（一般科目）：自然科学・応用科学, 2024年, 修士課程, 大学院共通科目
• 有機化学特論, 2024年, 修士課程, 総合化学院
• 生物化学Ａ（Ⅳ）, 2024年, 修士課程, 総合化学院
• 先端総合化学特論Ⅰ, 2024年, 博士後期課程, 総合化学院
• 総合化学特論II (Modern Trends in Organic Chemistry and Biological Chemistry), 2024年, 博士後期課程, 工学院
• 化学実験Ⅵ, 2024年, 学士課程, 理学部
• 化学実験Ｆ, 2024年, 学士課程, 理学部
• 有機化学Ⅱ, 2024年, 学士課程, 理学部
• 科学・技術の世界, 2024年, 学士課程, 全学教育

• カゴ型炭素骨格の高効率構築法に基づく高次構造天然物の全合成
  科学研究費助成事業
  01 Apr. 2024 - 31 Mar. 2027
  谷野 圭持
  日本学術振興会, 基盤研究(B), 北海道大学, 24K01477
• ペリ環状反応に基づくユニークな中員環骨格構築法：高次構造天然物合成への展開
  科学研究費助成事業 基盤研究(B)
  01 Apr. 2021 - 31 Mar. 2024
  谷野 圭持
  自然界には、様々な大きさの炭素環が互いに縮合した複雑な分子構造を持つ天然有機化合物が数多く存在する。それら天然物の化学合成は医薬品の開発にも繋がり、学術面のみならず社会的な要請にも応える重要な研究課題である。本研究の目的は、独自に開発した有機合成反応を駆使し、従来の方法では困難な中員環炭素骨格構築法を開発することにある。さらに、天然物合成への応用を通して、その有用性を実証する。
  １年目の実績として、脱離基として挙動するカルバマート基を導入した鎖状トリエン基質に強塩基を作用させることで、ヘプタトリエニルアニオンの生成に続く8π系電子環状反応が進行し、交差共役7員環トリエンが単一の生成物として得られることを明らかにした。ヘプタトリエニルアニオンの8π系電子環状反応は古くから知られているものの、生成する7員環ジエンが異性体混合物となる問題点などから、一般的な7員環構築法として確立されていなかったが、本業績はこの制約を打破するものである。
  さらに、アニオン安定化基を導入した基質トリエンの8π系電子環状反応を検討し、リン酸エステル基を導入した基質から、塩基性条件下での環化反応とアルデヒドとのワンポットHorner-Wadsworth-Emmons反応を経て、交差共役7員環トリエンを得る新反応の開発に成功した。これと同時に、基質両末端の置換基は、形成される7員環上では互いに隣接する炭素上に存在するが、それらの相対立体配置が基質の二重結合の立体配置を反映する「立体特異的な環化反応」であることを証明した。
  日本学術振興会, 基盤研究(B), 北海道大学, 21H01923
• 四級不斉炭素構築法の新展開：付加／転位反応による高次構造天然物の効率合成
  科学研究費補助金(基盤研究(B))
  2018 - 2020
  谷野 圭持
  文部科学省, Principal investigator, Competitive research funding
• 超微量生物機能性天然中分子の高効率合成
  科学研究費補助金(新学術領域研究(研究領域提案型))
  2015 - 2019
  谷野 圭持
  文部科学省, Principal investigator, Competitive research funding
• 炭素小員環化合物とヘテロ原子の複合利用による高次構造天然物の合成
  科学研究費補助金(基盤研究(B))
  2015 - 2017
  谷野 圭持
  文部科学省, Principal investigator, Competitive research funding
• Natural Product Synthesis by Utilizing Compact and Multifunctional Properties of Cyano Group
  Grants-in-Aid for Scientific Research
  2012 - 2014
  TANINO Keiji
  The synthetic studies on Tubiferal A, Azadirachtin, and Phorbol were carried out on the basis of new reactions utilizing alkanenitriles. The unique properties of a cyano group, which is sterically compact and linear in shape, were found to be advantageous for forming carbocyclic compounds possessing hindered carbon-carbon bonds. For example, construction of the 5-7 bicyclic skeleton of Phorbol was achieved by the divinylcyclopropane rearrangement reaction of a cyanocyclopropane derivative.
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, Principal investigator, Competitive research funding, 24350018
• Concise Total Synthesis of Polycyclic Bioactive Natural Products Based on New Integrated Reactions
  Grants-in-Aid for Scientific Research
  2009 - 2012
  TANINO Keiji
  In connection with the research directed toward total synthesis of polycyclic natural products, we became intrigued with higher order cycloaddition approach for constructing medium-sized carbocycles. The use of a dicobalt acetylene complex possessing a leaving group and a nucleophile moiety was effective for achieving the [6+2], [6+4], and [5+2] cycloaddition reactions. These cascade reactions proceed through generation of a dicobalt hexacarbonyl propargyl cation, intermolecular addition (Nicholas reaction), followed by intramolecular cyclization. The results led us to explore applications of these new cycloaddition reactions in total synthesis of natural products containing seven, eight, nine, or ten-membered carbocycles.
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area), Hokkaido University, Principal investigator, Competitive research funding, 21106010
• Synthetic Studies on Complex Terpenoids with Bioactivities as Lead Compounds of Agricultural Chemicals
  Grants-in-Aid for Scientific Research
  2009 - 2011
  TANINO Keiji
  Potato cyst nematode is a troublesome parasite that live on, and destroy, important vegetable plants including potatoes. We have achieved the first total synthesis of solanoeclepin A, the key hatch-stimulating substance for potato cyst nematode, through 52-step transformations. The synthetic solanoeclepin A was shown to stimulate the hatching activity at high dilution in water, and the present synthesis has the potential to contribute to the critical food supply issue.
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, Principal investigator, Competitive research funding, 21350021
• Studies Toward Total Synthesis of Polycyclic Natural Products with a Complex Chemical Structure and Distinctive Biological Properties
  Grants-in-Aid for Scientific Research(基盤研究(B))
  2007 - 2009
  Masaaki MIYASHITA; 谷野 圭持; 南雲 紳史; Keiji TANINO; Shinji NAGUMO
  Recently, there have been discovered an extremely small quantity of natural products with novel chemical structures and distinctive biological properties which have drawn much attention inside and outside the country, particularly, in relation to development of a new type of medicines. This research mainly aimed at chemical synthesis of the zoanthamine alkaloids that have exhibited potent biological and pharmacological activities. As a result, we achieved the first chemical syntheses of zoanthamine with powerful analgesic effects, and zoanthenol with potent antiplatelet activities on human ...
  Ministry of Education, Culture, Sports, Science and Technology, 基盤研究(B), 工学院大学, Coinvestigator not use grants, Competitive research funding, 19350027
• 生体機能分子の創製の研究統括
  科学研究費補助金(特定領域研究)
  2004 - 2008
  福山 透; 小林 資正; 佐々木 誠; 谷野 圭持; 菅 敏幸
  平成20年6月に、取りまとめの公開シンポジウムをタワーホール船堀(東京)にて実施した。このとき代表的な研究成果を中心に公開し、成果を社会に対して発信した。これらの研究成果は、生命現象の化学的解明に飛躍的な進展や新戦略による創薬にも直結するため、製薬に代表される産業界においても有用であり、公開シンポジウムでは企業の研究者も幅広く参加した。また、本特定領域研究では、各研究項目の計画研究班員と公募班員の間での緊密な共同研究体制を構築することを重要課題として掲げた。これまで、公開シンポジウムやHPにより研究者の相互の理解を深め、有機的連携と緊密な共同研究体制を構築した。現在までに、30組以上の領域内共同研究が進行中であり、成果があがりつつある。また、最終報告も平成21年3月に作成した。この最終報告書にはおのずと解決された問題と、さらに解決されなかった問題(既存の学術誌等には投稿できない)が例示されることとなるため、この方面の研究者にとって研究課題が容易に見つけ出せるバイブル的な存在になるように留意し整理した。また、班員、研究協力者、班友の業績を中心としたテキスト「天然物の全合成 : 2001〜2008」の編纂を行った。現在最終校正の段階にあり、平成21年中に発売可能な状態にある。本特定領域ではすでに50を超える生理活性天然物(生体機能分子)の全合成を達成している。それらを網羅する本書...
  文部科学省, 特定領域研究, 東京大学, Coinvestigator not use grants, Competitive research funding, 16073101
• 付加環化反応を基軸とする多置換中員環炭素骨格構築法の開発
  科学研究費補助金(特定領域研究)
  2004 - 2007
  谷野 圭持; 宮下 正昭; 吉村 文彦
  昨年度は、独自のシクロペンテンアヌレーション法および橋頭位アニオンを用いるA環部導入法を駆使し、ダイズシスト線虫孵化促進物質グリシノエクレピンAの不斉全合成を達成した。今年度はまず、この知見をさらに発展させて天然物グリシノエクレピンBの不斉全合成を目指した。本化合物はグリシノエクレピンAの類縁体であるが、D環上の側鎖にγ-ヒドロキシ-α,β-不飽和カルボン酸部位を有する点が異なる。この部位の立体選択的構築法を検討した結果、光学活性配位子を用いる不斉野崎-檜山-岸カップリング反応を用いることにより、世界初の不斉全合成を達成することができた。一方、昨年度から着手した高次構造天然物アザジラクチンの全合成研究においては、高度に縮環したEFG環部の効率的な合成法を検討した。その結果、Nazarov環化反応によりE環を、分子内ェーテル環化によりF環を、メチルチオ基を水銀塩で活性化する分子内グリコシル化反応によりG環を各々構築し、モデル化合物の効率的合成に成功した。今後は、この知見を既に確立したC8位四級不斉炭素の立体選択的構築法と組み合わせることで、アザジラクチンの全合成が達成する計画である。さらに、海洋産天然物スクレロフィチンAの全合成研究において、以下の画期的な進展があった。従来は、[6+4]型付加環化反応により構築した11-オキサビシクロ[6.2.1]ウンデカン骨格が、脱コバルト錯...
  文部科学省, 特定領域研究, 北海道大学, Principal investigator, Competitive research funding, 16073201
• Synthetic Studies of Polycyclic Natural Products with Unique Chemical Structures and Potent Biological Activities
  Grants-in-Aid for Scientific Research(基盤研究(B))
  2004 - 2005
  Masaaki MIYASHITA; 谷野 圭持
  (1)Aymmetric Total Syntheses of Norzoanthamine and ZoanthamineNorzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug. On the other hand, zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. The distinctive biological properties and novel chemical structures of this family of alkaloids make them extremely attractive targets for chemical synthesis. However, the chemical synthesis of the zoanthamine ...
  Ministry of Education, Culture, Sports, Science and Technology, 基盤研究(B), 北海道大学, Coinvestigator not use grants, Competitive research funding, 16350049
• Development of New Methods for Constructing Medium Sized Carbocycles by Using Acetylene Dicobalt Complexes
  Grants-in-Aid for Scientific Research(基盤研究(B))
  2002 - 2004
  Keiji TANINO
  (1)New aspects of [5+2] cycloaddition reactionsIn order to explore the scope and limitations of the [5+2] cycloaddition reaction using the five-carbon unit having an acetylene dicobalt complex moiety and an enol silyl ether moiety, the reactions with various electron rich olefins as well as aromatic compounds were examined. Although aromatic compounds including anisols and aniline derivatives gave no good results, the reaction with a siloxyallene derivative was found to give the desired seven-membered cycloadduct in good yield.(2)Development of the higher-order cycloaddition reactionsA new ...
  Ministry of Education, Culture, Sports, Science and Technology, 基盤研究(B), 北海道大学, Principal investigator, Competitive research funding, 14340191
• Development of Synthetic Methodologies for Acyclic Organic Molecules Having Multi-Chiral Centers and Their Application to Natural Product Synthesis
  Grants-in-Aid for Scientific Research(基盤研究(A))
  2000 - 2002
  Masaaki MIYASHITA; 谷野 圭持
  Development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers is one of the important research projects in modern synthetic organic chemistry in context with the chiral synthesis of biologically and medicinally important compounds. This research project was carried out aiming at the development of highly stereoselective synthetic methodologies for acyclic organic molecules having contiguous asymmetric centers using stereospecific substitution reactions of epoxides as synthetic strategy .when this grant was provided.(1) The C...
  Ministry of Education, Culture, Sports, Science and Technology, 基盤研究(A), 北海道大学, Coinvestigator not use grants, Competitive research funding, 12304042
• インゲノールの全合成研究
  科学研究費補助金(奨励研究(A))
  1998 - 1999
  谷野 圭持
  筆者は昨年度までに、コバルトアセチレン錯体部位を有するtrans-デカリノール誘導体の分子内環化反応およびエポキシアルコールの炭素骨格転位反応を経て新規なインゲナン誘導体を合成することに成功した。この化合物はインゲノールと等しいCD環部を有するのみならず、A環上の1位およびB環上の6位に各々酸素官能基を有する重要中間体である。今年度は、このインゲナン誘導体からインゲノールへの変換を実現するべく、まずA環の官能基化を検討した。すなわち、1位水酸基をケトンへと酸化した後、2位へのexo-メチレン基の導入および水素添加を経て2-メチル体を合成した。さらに、1位ケト基を還元して得たアルコールを脱水反応によりC(1)-C(2)オレフィンとした後、クロム酸を用いたアリル位の酸化反応により3位にケト基を導入した。最後に、DIBALを用いて3位ケト基を立体選択的に還元し、インゲノールのA環に存在するすべての官能基の導入を達成した。一方、これと並行してB環の官能基化についても以下の検討を行った。すなわち、6位水酸基をケトンへと酸化した後、塩基で処理して4位のメトキシ基をβ-脱離させ、共役エノンを得た。このものに塩基性過酸化水素を作用させて立体選択的にC(4)-C(5)エポキシドとした後、Peterson反応により6位ケト基をケテンジチオアセタールへと変換した。最後に、塩化銅で処理してエポキシド...
  文部科学省, 奨励研究(A), 東京工業大学->北海道大学, Principal investigator, Competitive research funding, 10750619
• 新有機反応メディア
  科学研究費補助金(重点領域研究, 特定領域研究(A))
  1997 - 1999
  吉田 潤一; 堀口 良昭; 澤村 正也; 岩澤 伸治; 大嶋 幸一郎; 神戸 宣明; 碇屋 隆雄; 谷野 圭持
  本研究では新化学現象・新反応の発見と開拓のために、反応の分子環境としての反応場、反応剤、反応媒体、反応手法などを反応メディアという観点から研究を行ってきた。とくに、電子移動反応場、高分子反応場、結晶反応場、ラジカル反応場、金属錯体反応場、特異条件反応場とそれらの境界領域について重点的に検討を行い、新現象・新反応の発見を目指して検討を行ってきた。その結果、多くの特筆すべき成果を得ることができた。以下に示す。電子移動反応場においては、活性種の生成条件を高度に制御することにより、生成した活性種を蓄え、それを結合生成反応に用いるというカチオンプール法を開拓し、炭素-炭素結合生成反応の新しい方法論を明らかにした。さらに、電解反応場と固体マトリックス反応場の組み合わせにより、高効率・高選択的な分子変換法を明らかにした。また、有機金属反応場、ラジカル反応場、カチオン反応場においては、新活性種や機能性反応場反応の構築などにおいて顕著な成果を上げることができた。媒体の研究においても注目すべき成果が得られた。すなわち、水中におけるラジカル反応において、従来の有機溶媒中の反応にみられない興味深い応性の変化や選択性の変化が観測されることを明らかにした。また、水中におけるイオン反応の促進効果を利用し、ラジカル反応とイオン反応を組み合わせる新しい反応系の開発をも明らかにした。さらに、超臨界流体における金...
  文部科学省, 重点領域研究, 特定領域研究(A), 京都大学, Coinvestigator not use grants, Competitive research funding, 09238102
• New Methodologies for Construction of Medium- and Large-sized Carbocycles
  Grants-in-Aid for Scientific Research(基盤研究(B))
  1996 - 1997
  Isao KUWAJIMA; 谷野 圭持
  The following synthetically useful methodologies have been developed by this research project.(1) The substrates such as 3- (alkylthio) -2- (siloxy) - and 3- (alkylthio) -2- (silylmethyl) allyl acetates have been shown as useful three carbon units for [3 + 2] cylopentanone and methylene cyclopentane annulation in the reactions with electron-rich olefins. It has also been proposed the high observed regioselectivity is due to thermodynamic control of this reaction, and excellent stereoselectivity observed in the reaction with vinylsulfides may be due to remarkable effect of sulfur having a la...
  Ministry of Education, Culture, Sports, Science and Technology, 基盤研究(B), 東京工業大学, Coinvestigator not use grants, Competitive research funding, 08454198
• Development of Selective C-C bond Farming ReactionsTotal Synthesis of Natural Products
  1997
  Competitive research funding
• イミンのエン反応を利用した高立体選択的含窒素化合物の合成研究
  科学研究費補助金(奨励研究(A))
  1995 - 1995
  谷野 圭持
  まず、2-(メチルチオ)クロチルシリルエーテルと芳香族鎖状イミンとのエン反応について検討を行った結果、窒素上にアルコキシカルボニル基を導入することでイミンの反応性が著しく向上し、良好な収率で目的とする付加体が得られることを見出した。本反応のジアステレオ選択性は高く、エン基質のZ体はsyn体を、またE体はanti体をそれぞれ選択的に与えた。一方、対応する脂肪族鎖状イミンは合成困難であったが、1,1-ビスカルバマートを等価体として用いることで、高立体選択的にエン反応が進行することを明らかにした。次に、環状イミンとの反応について検討を行い、5-アシロキシピロリドン誘導体をイミン等価体として用いることでピロリジン環上へのジアステレオ選択的な側鎖導入を実現した。さらに、本反応の不斉合成への応用を試み、光学活性な1-フェネチルアミンから誘導される出発原料を用いればジアステレオ面選択的付加が起こることを明らかにした。以上の反応によって得られるエン付加体は、アシル基で保護されたアミノ基およびエノールシリルエーテル部位を合わせ持つことから、含窒素複素環の前駆体として有用であることを示した。すなわち、付加体を酸で処理するとエノールシリルエーテル部位の加水分解および環化が進行し、ピロリジノール誘導体を与えるが、このもののエステル誘導体にルイス酸共存下、種々の求核試剤を作用させることにより、環骨格上...
  文部科学省, 奨励研究(A), 東京工業大学, Principal investigator, Competitive research funding, 07740489
• 高立体選択的エン反応の開発及び天然物合成への応用
  科学研究費助成事業
  1991 - 1991
  谷野 圭持
  日本学術振興会, 奨励研究(A), 東京工業大学, 03740271