Researcher Profile and Settings

Master

Affiliation (Master)

• Faculty of Science　Chemistry　Organic and Biological Chemistry

Affiliation (Master)

• Faculty of Science　Chemistry　Organic and Biological Chemistry

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Profile and Settings

Profile and Settings

• Name (Japanese)

  Suzuki

• Name (Kana)

  Takahiro

• Name

  200901092974213923

Alternate Names

http://kaken.nii.ac.jp/ja/r/80367052

Achievement

Research Interests

• 合成化学   有機化学   

Research Areas

• Nanotechnology/Materials / Synthetic organic chemistry
• Life sciences / Bioorganic chemistry
• Nanotechnology/Materials / Structural/physical organic chemistry
• Life sciences / Pharmaceuticals - chemistry and drug development

Research Experience

• 2014/03 - Today Hokkaido University Associate Professor
• 2013/04 - 2014/02 Waseda University
• 2009/04 - 2013/03 Tokyo University of Science Faculty of Pharmaceutical Sciences
• 2003/04 - 2005/03 Waseda University Faculty of Science and Engineering

Awards

• 2018/01 日本化学会北海道支部 日本化学会北海道支部奨励賞
   特異な構造の天然物の全合成と拡散的研究展開 

  受賞者: 鈴木孝洋
• 2016/10 Asian Core Program Lectureship Award from HongKong
   

  受賞者: 鈴木孝洋
• 2016/10 Asian Core Program Lectureship Award from China
   

  受賞者: 鈴木孝洋

Published Papers

• 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 2024/08/19
• 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 2193-5807 2024/06/10 

  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.
• 生合成経路を模倣するChloropupukeananin類の全合成

  Takahiro Suzuki

  Journal of Synthetic Organic Chemistry, Japan 82 (4) 0037-9980 2024/04/01
• A lipid index for risk of hyperlipidemia caused by anti-retroviral drugs

  Mari Shimura, Nobuyo Higashi-Kuwata, Asuka Fujiwara, Mai Taniguchi, Takayuki Ichinose, Fumie Hamano, Masaaki Uematsu, Takato Inoue, Satoshi Matsuyama, Takahiro Suzuki, Arun K. Ghosh, Hideo Shindou, Takao Shimuzu, Hiroaki Mitsuya

  Antiviral Research 2024/03
• Synthesis of dihydrotropone derivatives using an anionic 8π-electrocyclic reaction

  Ranmaru Kato, Takahiro Suzuki, Keiji Tanino

  Chemical Communications 2024
• Alcohol synthesis based on the SN2 reactions of alkyl halides with the squarate dianion

  Kazuto Sato, Tomoyuki Fujita, Takashi Takeuchi, Takahiro Suzuki, Kazutada Ikeuchi, Keiji Tanino

  Organic & Biomolecular Chemistry 2024
• Scope and limitations of absolute configuration determination of allenic natural products using the CCC stretching VCD signal.

  Tohru Taniguchi, Mutmainah, Shu Takimoto, Takahiro Suzuki, Soichiro Watanabe, Fuyuhiko Matsuda, Taiki Umezawa, Kenji Monde

  Organic & biomolecular chemistry 21 (3) 569 - 574 2023/01/18 

  The allene functional group in natural products isolated so far exists in a non-racemic form, but its axial chirality is difficult to elucidate. Allenes exhibit a characteristic antisymmetric CCC stretching mode at around 1950 cm-1, and their VCD properties have not been studied in detail. This work, for the first time, applied VCD spectroscopy to allenic natural products and allenic molecules with other asymmetric centers focusing on the antisymmetric CCC stretching mode. This vibrational mode yielded a negligibly weak VCD signal for several molecules, but in the presence of electron-withdrawing and/or conjugating substituents, it generated a stronger one. Its sign was found to be influenced by the nature of substituents. These findings should deepen the understanding of the VCD properties of the allene functional group and should be useful for future studies of chiral allenes.
• Total Synthesis of (+)-Coriamyrtin via a Desymmetric Strategy of a 1,3-Cyclopentanedione Moiety

  Kazutada Ikeuchi, Shota Haraguchi, Ryo Fujii, Hidetoshi Yamada, Takahiro Suzuki, Keiji Tanino

  2022/12/28 

  This paper describes the total synthesis of (+)-coriamyrtin, a picrotoxane-type sesquiterpene. The natural product is widely known as a neurotoxin of the Coriariaceae family and bears a highly functionalized cis-hydrindane skeleton. Despite being biologically and synthetically attractive molecule, only two examples of the total synthesis are reported to date. Our synthetic strategy involves the highly stereoselective construction of the cis-hydrindane skeleton via the desymmetric strategy of a 1,3-cyclopentanedione moiety using an intramolecular aldol reaction and elaborate functionalization of the cyclopentane ring in the bicyclic structure for the formation of the 1,3-diepoxide moiety of coriamyrtin. Our method could be applied to synthesize various natural products with similar bicyclic skeletons and to expand neurobiological studies using synthesized products.
• Synthesis of 2-alkyl-2-(2-furanyl)-1,3-cyclopentanediones

  Kazutada Ikeuchi, Yusuke Ozoe, Ranmaru Kato, Takahiro Suzuki, Keiji Tanino

  Synthesis 0039-7881 2022/12/27 

  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, we used 2-acylfuran derivatives 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 equivalents 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.
• Diastereoselective Synthesis of trans‐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 0947-6539 2022/12/18
• 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 2022/11/04
• Total Syntheses of Chloropupukeananin and Its Related Natural Products

  Takahiro Suzuki

  Organics 2022/09/09
• 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 2022/09/09 [Refereed][Not invited]
  
• Total Syntheses of Chloropupukeananin and Its Related Natural Products

  Takahiro Suzuki

  Organics 2022/09
• 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 1523-7060 2022/07/22
• 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 1523-7052 2021/12/17 [Refereed]
  
• Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-ring Compound

  Yuki Yukutake, Takahiro Hiramatsu, Ryusei Itoh, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino

  Synlett 33 (03) 296 - 300 0936-5214 2021/11/16 

  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.
• 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 1523-7060 2021/11/11
• Biomimetic Total Syntheses 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 0022-3263 2021/11/05
• Synthetic Studies of Daphniphyllum Alkaloids: A New Method for the Construction of [7-5-5] All-carbon Tricyclic Skeleton

  Jun-ichiro Kishi, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino

  Synlett 33 (02) 196 - 200 1437-2096 2021/10/29 

  Daphniphyllum alkaloids have a complex molecular structure; thus, 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 via the divinylcyclopropane rearrangement of a cyclopentenone derivative with a vinylcyclopropyl group at the β-position. After introducing a 2-iodoethyl group via a regioselective Michael addition with phenyl vinyl selenone, the [7-5-5] tricyclic system was formed by the intramolecular alkylation reaction of a cyclopentadienyl anion species.
• 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 1523-7060 2021/10/29
• 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 2021/09/02 

  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.
• Formal Total Synthesis of Atropurpuran

  Takahiro Suzuki, Takeshi Koyama, Kenta Nakanishi, Susumu Kobayashi, Keiji Tanino

  The Journal of Organic Chemistry 85 (15) 10125 - 10135 0022-3263 2020/08/07
• An Intermolecular [4+3] Cycloaddition Reaction Using 3-Hydroxy-2-pyrone Derivatives with an Oxyallyl Cation

  Takahiro Suzuki, Takamune Yanagisawa, Keiji Tanino

  HETEROCYCLES 99 (2) 848 - 848 0385-5414 2019 [Refereed][Invited]
  
• Asymmetric Total Synthesis of (-)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family

  Suzuki, Takahiro, Watanabe, Soichiro, Uyanik, Muhammet, Ishihara, Kazuaki, Kobayashi, Susumu, Tanino, Keiji

  Organic Letters American Chemical Society ({ACS}) 20 (13) 3919 - 3922 2018/07/06 [Refereed][Not invited]
  
• Enantioselective total synthesis of (+) -iso-A82775C

  Takahiro Suzuki

  Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 76 (5) 462 - 465 0037-9980 2018 [Refereed][Invited]
   

  (+) -Iso-A82775C is one of the proposed biosynthetic precursors of chloropupukeananin and an important intermediate for related bioactive natural products. The first enantioselective total synthesis of (+) -iso-A82775C toward the eventual biomimetic total synthesis of chloropupukeananin has been achieved. The key steps of the total synthesis are the enantioselective Diels-Alder reaction of 4-bromo-3-hydroxy-2-pyrone with methyl 2-chloroacrylate catalyzed by cinchona alkaloids and the anti-selective Cu-mediated S N2′ reaction to afford the axially chiral vinylallene moiety. Herein the details and inside stories are disclosed.
• Total synthesis of (+)-methynolide using a Ti-mediated aldol reaction of a lactyl-bearing oxazolidin-2-one, and a vinylogous Mukaiyama aldol reaction

  Takahiro Suzuki, Masataka Fujimura, Kazuhiro Fujita, Susumu Kobayashi

  TETRAHEDRON 73 (26) 3652 - 3659 0040-4020 2017/06 [Refereed][Invited]
   

  A highly convergent total synthesis of (+)-methynolide, based on two types of stereoselective aldol reaction, was achieved. The C1-C8 and C9-C11 fragments of (+)-methynolide were prepared by a vinylogous Mukaiyama aldol reaction using a vinyl ketene silyl N,O-acetal, and a Ti-mediated aldol reaction of a lactyl-bearing chiral oxazolidin-2-one, respectively. Yamaguchi esterification of both fragments and ring-closing metathesis afforded (+)-methynolide. (C) 2017 Elsevier Ltd. All rights reserved.
• 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 1523-7060 2017/02 [Refereed][Not invited]
   

  (+)-Iso-A82775C is a proposed biosynthetic precursor of the chloropupukeananin family and an important intermediate for related natural products. The first enantioselective total synthesis of (+)-iso-A82775C (18 steps, 2.2% overall yield) toward the eventual biomimetic total synthesis of chloropupukeananin is described. The key steps are (1) the enantioselective Diels Alder reaction of 4-bromo-3-hydroxy-2-pyrone with methyl 2-chloroacrylate using cinchonine as an organocatalyst and (2) the anti-selective Cu-mediated S(N)2' reaction to afford the axially chiral vinylallene moiety.
• Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei

  Shu Nishikori, Kenji Takemoto, Shinji Kamisuki, Syo Nakajima, Kouji Kuramochi, Senko Tsukuda, Masashi Iwamoto, Yuri Katayama, Takahiro Suzuki, Susumu Kobayashi, Koichi Watashi, Fumio Sugawara

  JOURNAL OF NATURAL PRODUCTS 79 (2) 442 - 446 0163-3864 2016/02 [Refereed][Not invited]
   

  New diazabicyclo[2.2.2]octane derivatives, peniciherquamides A-C (1-3), and a novel herqueinone derivative, neoherqueinone (5), were isolated from a fungal culture broth of Penicillium herquei. The structures of these novel compounds were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Four known compounds, preparaherquamide (4), peniciherqueinone (6), and herqueinone/isoherqueinone (7/7a), were also obtained. The isolated compounds were tested for anti hepatitis C virus (HCV) activity, and peniciherquamide C (3) was found to display an IC50 value of 5.1 mu M. To our knowledge, this is the first report of a diazabicyclo[2.2.2]octane derivative with anti-CV activity.
• A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

  Kenji Usui, Takahiro Suzuki, Masahisa Nakada

  TETRAHEDRON LETTERS 56 (10) 1247 - 1251 0040-4039 2015/03 [Refereed][Not invited]
   

  A highly stereoselective intramolecular Diels Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthetic study of spiroiridal triterpenoids: construction of functionalized spiro[4.5]decane skeleton using Claisen rearrangement of 2-(alkenyl)dihydropyran

  Noriyuki Takahashi, Keiji Tamura, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  TETRAHEDRON LETTERS 56 (2) 327 - 330 0040-4039 2015/01 [Refereed][Not invited]
   

  The spiroiridal triterpenoids show interesting biological activities, such as a piscicidal activity, PKC activation, and molluscicidal activity. Herein, the first synthesis of the functionalized spiro[4.5]decane skeleton of spiroiridal triterpenoids was accomplished. The characteristic features of the present synthesis are the Claisen rearrangement of 2-(alkenyl)dihydropyran developed by our group and the efficient transformation into the key intermediate (+)-6. (C) 2014 Elsevier Ltd. All rights reserved.
• Multimodal biopanning of T7 phage-displayed peptides reveals angiomotin as a potential receptor of the anti-angiogenic macrolide Roxithromycin

  Kaori Takakusagi, Yoichi Takakusagi, Takahiro Suzuki, Aya Toizaki, Aiko Suzuki, Yaichi Kawakatsu, Madoka Watanabe, Yukihiro Saito, Ryushi Fukuda, Atsuo Nakazaki, Susumu Kobayashi, Kengo Sakaguchi, Fumio Sugawara

  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 90 809 - 821 0223-5234 2015/01 [Refereed][Not invited]
   

  Roxithromycin (RXM) is a semi-synthetic fourteen-membered macrolide antibiotic that shows anti-angiogenic activity in solid tumors. In the present study, we conducted biopanning of T7 phage-displayed peptides either on a 96-well formatted microplate, a flow injection-type quartz-crystal microbalance (QCM) biosensor, or a cuvette-type QCM. RXM-selected peptides of different sequence, length and number were obtained from each mode of screening. Subsequent bioinformatics analysis of the RXM-selected peptides consistently gave positive scores for the extracellular domain (E458-T596) of angiomotin (Amot), indicating that this may comprise a binding region for RXM. Bead pull down assay and QCM analysis confirmed that RXM directly interacts with Amot via the screen-guided region, which also corresponds to the binding site for the endogenous anti-angiogenic inhibitor angiostatin (Anst). Thus, multimodal biopanning of T7PD revealed that RXM binds to the extracellular domain on Amot as a common binding site with Anst, leading to inhibition of angiogenesis-dependent tumor growth and metastasis. These data might explain the molecular basis underlying the mechanism of action for the anti-angiogenic activity of RXM. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis of Dibarrelane, a Dibicyclo[2.2.2]octane Hydrocarbon

  Takahiro Suzuki, Hiroshi Okuyama, Atsuhiro Takano, Shinya Suzuki, Isao Shimizu, Susumu Kobayashi

  JOURNAL OF ORGANIC CHEMISTRY 79 (6) 2803 - 2808 0022-3263 2014/03 [Refereed][Not invited]
   

  The synthesis of a novel hydrocarbon, dibarrelane, has been accomplished in 11 steps via an intramolecular REDDA reaction of a masked o-benzoquinone, followed by Clemmensen reduction and Barton decarboxylation. The twisted structure of the tetracyclic dibarrelane skeleton was also clarified via X-ray crystallography. Finally, it was proposed that dibarrelane has C-2 symmetry rather than C-2v symmetry.
• Total synthesis and anti-hepatitis C virus activity of MA026

  Satomi Shimura, Masahiro Ishima, Syo Nakajima, Toshitaka Fujii, Natsumi Himeno, Kentaro Ikeda, Jesus Izaguirre-Carbonell, Hiroshi Murata, Toshifumi Takeuchi, Shinji Kamisuki, Takahiro Suzuki, Kouji Kuramochi, Koichi Watashi, Susumu Kobayashi, Fumio Sugawara

  Journal of the American Chemical Society 135 (50) 18949 - 18956 0002-7863 2013/12/18 [Refereed][Not invited]
   

  The first total synthesis of MA026 and the identification of its candidate target protein for anti-hepatitis C virus activity are presented. MA026, a novel lipocyclodepsipeptide isolated from the fermentation broth of Pseudomonas sp. RtIB026, consists of a cyclodepsipeptide, a chain peptide, and an N-terminal (R)-3-hydroxydecanoic acid. The first subunit, side chain 2, was prepared by coupling fatty acid moiety 4 with tripeptide 5. The key macrocyclization of the decadepsipeptide at l-Leu10-d-Gln11 provided the second subunit, cyclodepsipeptide 3. Late-stage condensation of the two key subunits and final deprotection afforded MA026. This convergent, flexible, solution-phase synthesis will be invaluable in generating MA026 derivatives for future structure-activity relationship studies. An infectious hepatitis C virus (HCV) cell culture assay revealed that MA026 suppresses HCV infection into host hepatocytes by inhibiting the entry process in a dose-dependent manner. Phage display screening followed by surface plasmon resonance (SPR) binding analyses identified claudin-1, an HCV entry receptor, as a candidate target protein of MA026. © 2013 American Chemical Society.
• Deprotection of the Methoxymethyl Group on 3-Spiro-2-oxindole under Basic Conditions

  Atsuo Nakazaki, Kanako Iwakiri, Tomohiro Hirano, Takahiro Suzuki, Susumu Kobayashi

  CHEMICAL & PHARMACEUTICAL BULLETIN 61 (5) 587 - 591 0009-2363 2013/05 [Refereed][Not invited]
   

  Deprotection of a methoxymethyl (MOM) group on an oxindole nitrogen under basic conditions is demonstrated. The mechanisms of both the deprotection and the formation of N-methyloxindole were revealed by using deuterated NaOMe-MeOH in mechanistic studies.
• Unexpected Diels-Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin

  Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi

  ORGANIC LETTERS 15 (7) 1748 - 1751 1523-7060 2013/04 [Refereed][Not invited]
   

  The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.
• Synthetic Study of Kinamycins and Lomaiviticins

  SUZUKI Takahiro

  Journal of Synthetic Organic Chemistry, Japan 社団法人 有機合成化学協会 70 (10) 1069 - 1070 0037-9980 2012/10/01 [Refereed][Invited]
   

  Kinamycins and lomaiviticins are potent antiproliferative antimicrobial natural products possessing a unique diazotetrahydrobenzo[b]fluorene moiety. Biological and structural features of these compounds have attracted much attention from synthetic chemists. In this review, recent synthetic efforts toward lomaiviticins reported by Shair's group and Herzon's group are described.
• Synthetic Study of Pyrrocidines: First Entry to the Decahydrofluorene Core of Pyrrocidines

  Ryo Tanaka, Kentaro Ohishi, Noriyuki Takanashi, Tomohiko Nagano, Hiroshi Suizu, Takahiro Suzuki, Susumu Kobayashi

  ORGANIC LETTERS 14 (18) 4886 - 4889 1523-7060 2012/09 [Refereed][Not invited]
   

  The first synthesis of decahydrofluorene core 4 of pyrrocidines was accomplished. The cis,trans-fused tricyclic ring system was stereoselectively constructed via Diels-Alder reaction using two Danishefsky dienes.
• Pharmacological evaluation of a novel cyclic phosphatidic acid derivative 3-S-cyclic phosphatidic acid (3-S-cPA)

  Emi Nozaki, Mari Gotoh, Ryo Tanaka, Masaru Kato, Takahiro Suzuki, Atsuo Nakazaki, Harumi Hotta, Susumu Kobayashi, Kimiko Murakami-Murofushi

  BIOORGANIC & MEDICINAL CHEMISTRY 20 (10) 3196 - 3201 0968-0896 2012/05 [Refereed][Not invited]
   

  Cyclic phosphatidic acid (cPA) is a naturally occurring phospholipid mediator possessing cyclic phosphate ring, which is necessary for its specific biological activities. To stabilize cyclic phosphate ring of cPA, we synthesized a series of cPA derivatives. We have shown that racemic 3-S-cPA, with a phosphate oxygen atom replaced with a sulfur atom at the sn-3, was a more effective autotaxin (ATX) inhibitor than cPA. In this study, we showed that racemic 3-S-cPA also had potent biological activities such as inhibition of cancer cell migration, suppression of the nociceptive reflex, and attenuation of ischemia-induced delayed neuronal cell death in the hippocampal CA1. Moreover, we synthesized both enantiomers of palmitoleoyl derivative of 3-S-cPA, and found that the chirality of 3-S-cPA is not involved in ATX inhibition. Based on these findings, racemic 3-S-cPA is suggested as an effective therapeutic compound like cPA. (C) 2012 Elsevier Ltd. All rights reserved.
• Determination of the Absolute Structure of (+)-Akaterpin

  Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken-ichi Takao, Kazuo Umezawa, Susumu Kobayashi

  CHEMICAL & PHARMACEUTICAL BULLETIN 60 (1) 137 - 143 0009-2363 2012/01 [Refereed][Not invited]
   

  We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of beta,gamma-unsaturated ketone (+/-)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (-)-1 with that of natural akaterpin.
• Concise Total Synthesis of (-)-Myxalamide A

  Kazuhiro Fujita, Ryosuke Matsui, Takahiro Suzuki, Susumu Kobayashi

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 (29) 7271 - 7274 1433-7851 2012 [Refereed][Not invited]
  
• Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC

  Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken-ichi Takao, Kazuo Umezawa, Susumu Kobayashi

  TETRAHEDRON LETTERS 52 (38) 4961 - 4964 0040-4039 2011/09 [Refereed][Not invited]
   

  We describe the first total synthesis and structural determination of akaterpin, an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include a regio- and stereoselective C-alkylation at the angular C1' position and an exo-selective intermolecular Diels-Alder reaction. The relative stereochemistry was determined by a comparison of the NMR spectra of synthetic akaterpin with those of natural akaterpin. (C) 2011 Elsevier Ltd. All rights reserved.
• Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

  Ryo Tanaka, Masaru Kato, Takahiro Suzuki, Atsuo Nakazaki, Emi Nozaki, Mari Gotoh, Kimiko Murakami-Murofushi, Susumu Kobayashi

  BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 21 (14) 4180 - 4182 0960-894X 2011/07 [Refereed][Not invited]
   

  The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA. (C) 2011 Elsevier Ltd. All rights reserved.
• Different Modes of Cyclization in Zoanthamine Alkaloid System, Bisaminal versus Spiroketal Formation

  Takahiro Nakajima, Daisuke Yamashita, Kaname Suzuki, Atsuo Nakazaki, Takahiro Suzuki, Susumu Kobayashi

  ORGANIC LETTERS 13 (12) 2980 - 2983 1523-7060 2011/06 [Refereed][Not invited]
   

  Bisaminal cyclization in the zoanthamine alkaloid system was strongly affected by the stereochemistry of the C4 methyl. While cyclization of the (4S)-methyl precursor gave only a bisaminal compound, cyclization of the (4R)-methyl isomer produced both spiroketal and bisaminal products.
• Enantioselective Total Synthesis of (-)-FR182877

  Natsumi Tanaka Suzuki, Takahiro Suzuki, Takehiko Matsumura, Yousuke Hosoya, Tomoyuki Nakazato, Masahisa Nakada

  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 69 (6) 646 - 660 0037-9980 2011/06 [Refereed][Not invited]
   

  An enantioselective total synthesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenic centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membered F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the alpha-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.
• Stereoselective Vinylogous Mukaiyama Aldol Reaction of alpha-Haloenals

  Yoichi Iwasaki, Ryosuke Matsui, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  CHEMICAL & PHARMACEUTICAL BULLETIN 59 (4) 522 - 524 0009-2363 2011/04 [Refereed][Not invited]
   

  We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of alpha-haloenals. Contrary to the simple alpha,beta-unsaturated aldehyde, alpha-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of alpha-haloenals.
• The second generation synthesis of (+)-pseudodeflectusin

  Yuna Sato, Kouji Kuramochi, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  TETRAHEDRON LETTERS 52 (5) 626 - 629 0040-4039 2011/02 [Refereed][Not invited]
   

  The second generation synthesis of (+)-pseudodeflectusin (1), a potential antitumor agent, has been achieved. The key synthetic step is the cascade reaction involving Diels-Alder reaction, lactonization, and decarboxylation to give cycloadduct 6 with complete regioselectivity in good yield. We found that NaH is the best base to facilitate the Diels-Alder reaction of hydroxypyrone 7 with alkyne 8. The present synthetic route enables the total synthesis of (+)-1 in only five-steps from the known compounds 7 and 8. (C) 2010 Elsevier Ltd. All rights reserved.
• A Second-Generation Formal Synthesis of (+)-Haplophytine

  Weiwei Tian, Lohitha Rao Chennamaneni, Takahiro Suzuki, David Y-K Chen

  EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (6) 1027 - 1031 1434-193X 2011/02 [Refereed][Not invited]
   

  In this article, a Lewis acid mediated 1,4-addition/formal [3+2] cycloaddition reaction engaging functionalized beta-carboline and 1,4-benzoquinone has been demonstrated. Application of this developed technology facilitated the construction of the challenging C-9'-C-15 quaternary center linkage in the dimeric indole alkaloid, haplophytine, and enabled the preparation of an advanced key intermediate en route to the total synthesis of this historical natural product.
• Total Synthesis of (+)-Nafuredin-gamma Using a Highly Stereoselective Ti-Mediated Aldol Reaction

  Yuta Onodera, Takahiro Suzuki, Susumu Kobayashi

  ORGANIC LETTERS 13 (1) 50 - 53 1523-7060 2011/01 [Refereed][Not invited]
   

  An efficient total synthesis of (+)-nafuredin-gamma has been achieved in 10 steps from (E)-3-(tributylstannyl)propenal. The synthesis features direct construction of an anti-1,2-diol moiety via a Ti-mediated aldol reaction of lactyl derivative and rapid fragment assembly, which relied on well-established Pd chemistry.
• A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels-Alder Reaction

  Takahiro Suzuki, Aya Sasaki, Naoki Egashira, Susumu Kobayashi

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 50 (39) 9177 - 9179 1433-7851 2011 [Refereed][Not invited]
  
• Convergent Total Synthesis of (+)-TMC-151C by a Vinylogous Mukaiyama Aldol Reaction and Ring-Closing Metathesis

  Ryosuke Matsui, Kentaro Seto, Yttna Sato, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 50 (3) 680 - 683 1433-7851 2011 [Refereed][Not invited]
  
• Concise Approach to Pupukeanane Skeleton: Synthetic Study of Chloropupukeananin

  Takahiro Suzuki, Susumu Kobayashi

  ORGANIC LETTERS 12 (13) 2920 - 2923 1523-7060 2010/07 [Refereed][Not invited]
   

  A concise synthesis of a highly functionalized chloropupukeananin (1) skeleton via a reverse electron-demand Diels-Alder reaction and intramolecular carbonyl-ene reaction sequence based on our proposed biosynthetic pathway is described.
• Second-generation total synthesis of (-)-diversifolin

  Kazuma Tsuboi, Tomoaki Nakamura, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  TETRAHEDRON LETTERS 51 (14) 1876 - 1879 0040-4039 2010/04 [Refereed][Not invited]
   

  A second-generation total synthesis of (-)-diversifolin has been achieved by a more straightforward strategy. involving a highly stereochemistry-dependent 10-membered ring-closing metathesis and a stereoselective dihydroxylation/lactone transposition sequence. Compared to Our previous synthesis, the present synthesis is improved in the yield of the key intermediate 2 (20% in 12 steps from diol 8). (C) 2010 Elsevier Ltd. All rights reserved.
• Unusual E-Selective Ring-Closing Metathesis To Form Eight-Membered Rings

  Ryosuke Matsui, Kentaro Seto, Kazuhiro Fujita, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 49 (52) 10068 - 10073 1433-7851 2010 [Refereed][Not invited]
  
• Asymmetric total synthesis of (+)-carneic acid A and structure revision of its natural form

  Shuhei Yamakoshi, Nobuyuki Hayashi, Takahiro Suzuki, Masahisa Nakada

  TETRAHEDRON LETTERS 50 (38) 5372 - 5375 0040-4039 2009/09 [Refereed][Not invited]
   

  This Letter describes the asymmetric total synthesis of (+)-carneic acid A via the stereoselective IMDA reaction of (E,E,E)-triene, which was prepared from the commercially available methyl (S)-3-hydroxy-2-methylpropionate. By this asymmetric total synthesis, we verified that the reported absolute structure of naturally occurring carneic acid A must be revised. (C) 2009 Elsevier Ltd. All rights reserved.
• Total Synthesis of (-)-FR182877 through Tandem IMDA-IMHDA Reactions and Stereoselective Transition-Metal-Mediated Transformations

  Natsumi Tanaka, Takahiro Suzuki, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48 (14) 2580 - 2583 1433-7851 2009 [Refereed][Not invited]
  
• Total Synthesis of (+)-Haplophytine

  K. C. Nicolaou, Stephen M. Dalby, Shuoliang Li, Takahiro Suzuki, David Y-K. Chen

  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 48 (41) 7616 - 7620 1433-7851 2009 [Refereed][Not invited]
  
• Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction

  Nobuyuki Hayashi, Takahiro Suzuki, Kenji Usui, Masahisa Nakada

  TETRAHEDRON 65 (4) 888 - 895 0040-4020 2009/01 [Refereed][Not invited]
   

  This manuscript describes an alternative synthetic approach for (+)-phomopsidin, which shows strong inhibitory activity against the assembly of microtubule proteins. We observed that the TADA reaction of the macrolactone 5 with the reversed C11 configuration provided the desired cycloadduct 6 in 86% yield with excellent stereoselectivity (dr=16:1). Luche reduction of the ketone derived froth the major product of the TADA reaction resulted in a 91% yield with excellent stereoselectivity (dr=21:1), and the major product was Successfully converted to the known compound in the previously reported total synthesis of (+)-phomopsidin, thereby accomplishing the formal total synthesis of (+)-phomopsidin. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemical synthesis of the GHIJKLMNO ring system of maitotoxin

  K. C. Nicolaou, Michael O. Frederick, Antonio C. B. Burtoloso, Ross M. Denton, Fatima Rivas, Kevin P. Cole, Robert J. Aversa, Romelo Gibe, Taiki Umezawa, Takahiro Suzuki

  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130 (23) 7466 - 7476 0002-7863 2008/06 [Refereed][Not invited]
   

  As the largest secondary metabolite to be discovered as of yet, the polyether marine neurotoxin maiitotoxin constitutes a major structural and synthetic challenge. After its originally proposed structure (1) had been questioned on the basis of biosynthetic considerations, we provided computational and experimental support for structure 1. In an effort to provide stronger experimental evidence of the molecular architecture of maitotoxin, its GHIJKLMNO ring system 21 was synthesized. The (13)C NMR chemical shifts of synthetic 3 matched closely those corresponding to the same domain of the natural product providing strong evidence for the correctness of the originally proposed structure of maitotoxin (1).
• Catalytic asymmetric Nozaki-Hiyama reactions with a tridentate Bis(oxazolinyl)carbazole ligand

  Masahiro Inoue, Takahiro Suzuki, Akihiro Kinoshita, Masahisa Nakada

  CHEMICAL RECORD 8 (3) 169 - 181 1527-8999 2008 [Refereed][Not invited]
   

  Nozaki-Hiyama reactions are powerful Cr-II-mediated C-C bond-forming reactions conducted under mild conditions that show excellent compatibility with various functional groups. Therefore, Nozaki-Hiyama reactions have been utilized for many total syntheses of complex natural products, but at least two equivalents of Cr-II salt are required to complete the reaction because Cr-II salt is a one-electron donor. In 1996, however, the quantity of Cr-II salts required was successfully reduced by a catalytic redox system reported by Furstner and Shi. Since the report by Furstner, the catalytic asymmetric Nozaki-Hiyama reactions have attracted attention because they would allow control over enantioselectivity, thereby further enhancing the versatility of Nozaki-Hiyama reactions. In this review, we describe the development of a tridentate bis(oxazolinyl)carbazole ligand for the catalytic asymmetric Nozaki-Hiyama allylation, methallylation, propargylation, and allenylation. Also described are their successful applications to the highly stereoselective construction of the side chain of calcitriol lactone, as well as structure elucidation and the enantioselective first total synthesis of the potent 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors, FR901512 and FR901516. (C) 2008 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.
• Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (2)

  Natsumi Tanaka, Takahiro Suzuki, Yosuke Hosoya, Masahisa Nakada

  TETRAHEDRON LETTERS 48 (37) 6488 - 6492 0040-4039 2007/09 [Refereed][Not invited]
   

  Construction of the ABCD ring system of (-)-FRI 82877 via the intramolecular Diels-Alder (IMDA) reaction and the highly diastereoselective intramolecular hetero-Diels-Alder (IMHDA) reaction is described. The IMHDA reactions of the substrates incorporating the oxabutadiene with the E- or Z-alkene were examined, revealing that the sole product was obtained from both substrates and the E-alkene geometry was found to be crucial to obtaining the desired product. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (1)

  Takahiro Suzuki, Natsumi Tanaka, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

  TETRAHEDRON LETTERS 48 (37) 6483 - 6487 0040-4039 2007/09 [Refereed][Not invited]
   

  Construction of the ABCD ring system of (-)-FR182877 via the highly diastereoselective intramolecular Diels-Alder (I MDA) reaction is described. The IMDA reaction of the oj-unsaturated aldehyde generated in situ from the corresponding acetal successfully provided the desired product 14 possessing the AB ring system as the single diastereomer. The CD ring system was constructed by the subsequent IMHDA reaction and the additional experiment suggested that the diastereoselectivity of the IMHDA reaction could be related to the EIZ geometry of alkene 17, which was generated in situ from 16. (c) 2007 Elsevier Ltd. All rights reserved.
• Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes

  T Suzuki, N Tanaka, T Matsumura, Y Hosoya, M Nakada

  TETRAHEDRON LETTERS 47 (10) 1593 - 1598 0040-4039 2006/03 [Refereed][Not invited]
   

  The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (EEE)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton. (c) 2006 Elsevier Ltd. All rights reserved.
• First total synthesis of antimitotic compound, (+)-phomopsidin

  T Suzuki, K Usui, Y Miyake, M Namikoshi, M Nakada

  ORGANIC LETTERS 6 (4) 553 - 556 1523-7060 2004/02 [Refereed][Not invited]
   

  The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-alpha-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.
• New asymmetric tridentate carbazole ligand: Its preparation and application to Nozaki-Hiyama allylation

  T Suzuki, A Kinoshita, H Kawada, M Nakada

  SYNLETT (4) 570 - 572 0936-5214 2003/03 [Refereed][Not invited]
   

  The manuscript describes our studies on a newly designed tridentate ligand. The new ligand 1 was successfully synthesized, and it was found that the asymmetric catalysis of Nozaki-Hiyama allylation with ligand 1 affords the product with good enantioselectivity in high yield.
• Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand

  M Inoue, T Suzuki, M Nakada

  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 125 (5) 1140 - 1141 0002-7863 2003/02 [Refereed][Not invited]
  
• Synthetic studies on FR182877: an asymmetric synthesis of the AB ring moiety of FR182877 via a diastereoselective intramolecular Diels-Alder reaction

  T Suzuki, M Nakada

  TETRAHEDRON LETTERS 43 (18) 3263 - 3267 0040-4039 2002/04 [Refereed][Not invited]
   

  An asymmetric synthesis of the AB ring moiety of FR182877. possessing semen asymmetric centers. via a diastereoselective IMDA reaction is described, (C) 2002 Elsevier Science Ltd. All rights reserved.

MISC

• (+)-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
• 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
• 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
• 付加環化反応を基盤とした特異な環構造を有するテルペノイドの全合成研究

  鈴木孝洋  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  61st-  2017
• 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
• 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
• 抗ウイルス活性を有する新規環状デプシペプチドMA026の合成研究と標的分子の探索

  志村聡美, 中嶋翔, 中嶋翔, 藤井俊孝, 池田健太郎, IZAGUIRRE-CARBONELL Jesus, 石間正浩, 竹内倫文, 紙透伸治, 鈴木孝洋, 倉持幸司, 渡士幸一, 渡士幸一, 小林進, 菅原二三男  日本農芸化学会大会講演要旨集(Web)  2014-  2014
• Total Synthesis and Phage Display Screening to identify the target of MA026, a Novel Antiviral Lipocyclodepsipeptide

  Shimura Satomi, Ishima Masahiro, Ota Ikue, Tsutsui Etsuko, Kamisuki Shinji, Murata Hiroshi, Yamazaki Takayuki, Suzuki Takahiro, Kuramochi Koji, Takeuchi Toshifumi, Kobayashi Susumu, Sugawara Fumio  Symposium on the Chemistry of Natural Products, symposium papers  55-  (0)  2013  [Not refereed][Not invited]
   

  <p> MA026, a novel lipocyclodepsopeptide, was isolated from the fermentation broth of Pseudomonas sp. RtIB026 found in digestive tracts of rainbow trout. This natural product exhibits antiviral activity against infectious hematopoietic necrosis virus (IHNV) and several enveloped viruses. MA026 has a potential to create a novel antiviral drug and more biological characterizations are required. To conduct further studies to reveal the mode of action, a flexible chemical synthesis and modifications are essential. Herein, we provide the first total synthesis of MA026 and phage display screening to identify the target. MA026 consists of cyclodepsipeptide, chain peptide and N-terminal (R)-3-hydroxydecanoic acid. To maximize the convergency, MA026 was divided into two key segments, side chain 2 and cyclodepsipeptide 3. Key to the preparation of 3 was the macrocyclization of decadepsipeptide which relies on the macrocyclization site. Two macrocyclization sites were examined and the macrocyclization at D-Gln¹¹-L-Leu¹² furnished cyclodepsipeptide 3 successfully. To reveal the mechanism of antiviral activity, we synthesized biotinylated MA026 and MA026-immobilized PEGA resins. Phage display screenings using these probes were performed to afford peptide sequences that would interact with MA026.</p>
• 縮環系骨格の構築法を基にした天然物の合成

  鈴木 孝洋  上原記念生命科学財団研究報告集  27-  1  -6  2013  [Not refereed][Not invited]
  
• P-25 Synthetic Study of Pyrrocidine B(Poster Presentation)

  Tanaka Ryo, Ohishi Kentaro, Takanashi Noriyuki, Nagano Tomohiko, Suizu Hiroshi, Suzuki Takahiro, Kobayashi Susumu  天然有機化合物討論会講演要旨集  (54)  339  -344  2012/09/01  [Not refereed][Not invited]
   

  In 2002, pyrrocidine A and B were isolated from the fermentation broth of a fungus, LL-Cyan 426, as antimicrobial agents against Gram-positive bacteria including drug-resistant strains. Structural features of pyrrocidines are tricyclic decahydrofluorene core (ABC-ring) and 13-membered macrocycle containing para-substituted aryl ether moiety. The complex molecular architecture of these compounds makes them very attractive target molecules for total synthesis. We report herein the stereoselective synthesis of decahydrofluorene 21 which provides the first entry to the ABC-ring moiety of pyrrocidines. The synthesis of 21 commenced with the construction of the C-ring moiety. The cyclic carbon skeleton was synthesized via Diels-Alder reaction between dimethyl-substituted Danishefsky-Yan diene 7 and trisubstituted alkene 8 to afford a diastereomeric mixture of cyclohexenone 10a-b. The ketone 11a possessing the desired configuration was mainly obtained by thermal epimerization of the diastereomeric mixture of 11a-c. Ring-closing metathesis reaction of diene 15, followed by Dess-Martin oxidation afforded the cyclic dienophile 16. Diels-Alder reaction between Danishefsky-Kitahara diene 5 and bicycloenone 16, and the sequential acidic treatment gave diketone 4, establishing the tricyclic carbon framework of 21. Owing to the inherent convex-face selectivity of cis-fused bicyclic AB-ring moiety of 4, nitrile 19 was stereoselectively synthesized in several steps. Vinyl group was introduced to 4 from concave face selectively, avoiding the adjacent cyano group, in two steps to afford ketone 20. The reduction of ketone group from convex face of 20, followed by Chugaev elimination furnished decahydrofluorene 21.
• Synthetic studies of MA026, A novel antiviral lipocyclodepsipeptide

  S. Shimura, M. Ishima, Ota, I, E. Tsutsui, S. Kamisuki, H. Murata, T. Yamazaki, T. Suzuki, K. Kuramochi, T. Takeuchi, K. Watashi, S. Kobayashi, F. Sugawara  PLANTA MEDICA  78-  (11)  1283  -1283  2012/08  [Not refereed][Not invited]
  
• P-8 Synthetic Study of Atropurpuran(Poster Presentation)

  Suzuki Takahiro, Sasaki Aya, Kobayashi Susumu  天然有機化合物討論会講演要旨集  (53)  505  -510  2011/09/02  [Not refereed][Not invited]
   

  In 2009, Wang and colleagues reported the isolation of a structurally unique non-alkaloidal diterpene, atropurpuran, from Aconitum hemsleyanum var. atropurpureum. The structure of atropurpuran features an unprecedented cage-like skeleton consisting of five six-membered rings. Intriguingly, B, C, D, and E ring constitute the tetracyclo[5.3.3.0^<4'9>.0^<4'12>]tridecane skeleton into which two bicyclo[2.2.2]octane are comprised. Despite of these biosynthetically and structurally intriguing properties of tetracyclo[5.3.3.0^<4'9>.0^<4'12>]tridecane skeleton, no synthetic effort has been reported so far. Herein, we report the first entry for the construction of tetracyclic skeleton and the pentacyclic carbon framework of atropurpuran via an intramolecular reverse electron-demand Diels-Alder (REDDA) reaction of masked o-benzoquinone (MOB). The preparation of REDDA precursor was started from o-eugenol 1. Tetralone 4 was successfully converted to ketone 7. Reduction of ketone 7 with DIBAL, silyl etherification, followed by oxidation with Phl(OAc)_2 afforded REDDA precursor 10d. The REDDA reaction of silyl ether 10d (180℃, 1h) afforded tetracyclic 11d in high yield almost as a single diastereomer. Next, we proceeded to the construction of pentacyclic skeleton toward the total synthesis of atropurpuran. Addition of allylmagnesium bromide to ketone 7, ring-closing metathesis gave tricyclic 15. Oxidation of tricyclic 15 with Phl(OAc)_2 and followed by REDDA reaction of resulting MOB was achieved to construct the pentacyclic 14. Finally, hydrogenation of 15 and subsequent dehydration (Tf_2O, pyridine) afforded 16 to complete the construction of the pentacyclic framework of atropurpuran.
• P-62 Synthetic Studies of MA026(Poster Presentation)

  Shimura Satomi, Ishima Masahiro, Ota Ikue, Tsutsui Etsuko, Kamisuki Shinji, Murata Hiroshi, Yamazaki Takayuki, Suzuki Takahiro, Kuramochi Koji, Takeuchi Toshifumi, Kobayashi Susumu, Sugawara Fumio  天然有機化合物討論会講演要旨集  (53)  667  -672  2011/09/02  [Not refereed][Not invited]
   

  MA026, a novel lipocyclodepsipeptide, exhibits selective antiviral activity against enveloped viruses such as influenza and herpes. An antiviral compound with complex depsipeptide structure like MA026 is scarce, and MA026 has the potential to inhibit viral infections with a novel mechanism. However, the availability of MA026 from natural resources is limited, therefore, the chemical synthesis is essential to accomplish the biological investigation. Here, we present synthetic studies to establish an efficient synthetic pathway to MA026. MA026 consists of (3R)-hydroxydecanoic acid, linear peptide six amino acids and cyclodepsipeptide eight amino acids. Nine of the amino acids posses the D-configuration. The retrosynthetic analysis of MA026 (1) is shown in Figure 2. MA026 was devided into three key segments to maximize the convergency : branched cyclic depsipeptide 2, tripeptide 3 and fatty acid moiety 4. Key to the total synsthesis of MA026 is the macrocyclization of depsipeptide, so we chose two macrocyclization sites, (A) D-Val - D-Leu and (B) L-Leu - D-Gln. Protected amino acids were condensed to gave tripeptide 3. Fatty acid moiety 4 was synthesized from n-octylaldehyde through samarium mediated Reformatsky reaction. The macrocyclization substrate 5 was prepared by the condensation of peptide fragments. Then, 5 was cyclized and the formation of branched cyclic peptide 2 was confirmed by mass spectorometry, however, the 2 was not obtained as a single compound. Five dipeptides were condensed to gave the macrocyclization substrate 6. Attempts to cyclize the precursor 6 is in progress.
• 2カルバ環状ホスファチジン酸光学異性体の合成とその生理作用の検討

  野崎 絵美, 後藤 真里, 堀田 晴美, 花澤 修和, 鈴木 孝洋, 小林 進, 室伏 きみ子  脂質生化学研究  53-  264  -266  2011/04/28  [Not refereed][Not invited]
  
• 抗腫瘍活性天然ポリケチド(+)-TMC-151Cの収束的全合成

  松井亮介, 瀬戸健太郎, 佐藤優奈, 藤田和弘, 鈴木孝洋, 中崎敦夫, 小林進  日本化学会講演予稿集  91st-  (4)  2011
• 28-Deacetylbelamcandalの合成研究

  高梨憲幸, 田村圭司, 邊見和輝, 鈴木孝洋, 中崎敦夫, 小林進  反応と合成の進歩シンポジウム講演要旨集  37th-  2011
• Design and synthesis of molecular probe for identifying intracellular protein target

  Aya Toizaki, Aiko Suzuki, Atsuo Nakazaki, Takahiro Suzuki, Yoichi Takakusagi, Fumio Sugawara, Kengo Sakaguchi, Susumu Kobayashi  International Symposium on Technologies against Cancer (ISTC2011)  2011  [Not refereed][Not invited]
  
• Synthetic Study on 28-Deacetylbelamcandal

  Takanashi Noriyuki, Tamura Keiji, Henmi Kazuki, Suzuki Takahiro, Nakazaki Atsuo, Kobayashi Susumu  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  37-  (0)  77  -77  2011  [Not refereed][Not invited]
   

  A spiroiridal triterpenoid, 28-Deacetylbelamcandal was isolated from the rhizomes of <I>Belamcanda chinensis</I> in 1991. This natural product possesses a spiro[4.5]decane framework including five contiguous stereogenic centers and a tetrasubstituted olefin.<BR>Our strategy towards 28-Deacetylbelamcandal features Claisenrearrangement in alkenyl dihydropyran system for construction of a highly functionalized spiro[4.5]decane framework and stereoselective synthesis of tetrasubstituted olefin via intramolecular Heck reaction, subsequent deprotonation at bisallylic position and Rubottom oxidation.<BR>Alkenyl dihydropyran was prepared in 8 steps involving asymmetric aldol reaction and acid-catalyzed cyclization. The Claisen rearrangement (in triglyme, 0.05 M, 230 <SUP>o</SUP>C, 4 hr.) gave the desired product in 84% yield. Conversion of the Claisen product to the precursor for Heck reaction is currently under way.
• Synthetic Study of Chloropupukeananin

  Suzuki Takahiro, Miyajima Yuria, Suzuki Kaname, Koshimizu Masaki, Kobayashi Susumu  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  37-  (0)  51  -51  2011  [Not refereed][Not invited]
   

  Chloropupukeananin (<B>1</B>) was isolated from <I>Pestalotiopsis fici</I> by Che and colleagues as a new inhibitor against HIV-1 replication. The array of functional groups in a rigid tricyclic structure of <B>1</B> has provided us with a strong motive to construct the pupukeanane core based on biosynthetic hypothesis. We proposed a biosynthetic pathway for chloropupukeananin via maldoxin involving a reverse electron-demand Diels-Alder (REDDA) reaction and an intramolecular carbonyl-ene reaction. Herein, we report the investigation of REDDA and carbonyl-ene reaction with a model of maldoxin and vinylallene.<BR>The precursors of REDDA were subjected to high pressure conditions to give a major product and other isomers. The X-ray crystallographic analysis of the major product revealed that the precursors underwent the REDDA reaction and the intramolecular carbonyl-ene reaction to construct the pupukeanane core in a single operation.
• Total Synthesis of (+)-TMC-151C Using Vinylogous Mukaiyama Aldol Reaction and Ring Closing Metathesis

  Matsui Ryosuke, Seto Kentaro, Sato Yuna, Fujita Kazuhiro, Suzuki Takahiro, Nakazaki Atsuo, Kobayashi Susumu  天然有機化合物討論会講演要旨集  (52)  13  -18  2010/09/01  [Not refereed][Not invited]
   

  We have previously developed a highly stereoselective vinylogous Mukaiyama aldol reaction (VMAR) usin gvinylketene silyl N,O-acetal 1, which provides a unique and remarkable entry to a remote asymmetric induction. From a synthetic point of view, this method can directly afford th anti-δ-hydroxy-α,γ-dimethol-α,β-unsaturated carbonyl unit, which is seen in many naturally occurring products. In fact, VMAR has successfully been utilized in the total syntheses of various biologically active compounds by many groups including us. Se envisioned that the VMAR would be an efficient and powerful methodology for the synthesis of (+)-TMC-151C (2). This compound was isolated from Gliocladium sp. by the research group of Tanabe Seiyaku in 1999, and it shows the cytotoxicity to wide-rangingg tumor cell lines, such as HCT-116, B16 and HeLa. The structural significance as well as the biological property has stimulated the synthesis of TMC-151C (2). Herein, we report the first total synthesis of (+)-TMC-151C (2) using VMAR and Ring-Closing Metathesis (RCM) via a highly convergent synthetic route. Characteristic features of the present synthesis include: 1) the construction of C_1-C_5 segmetn and C_9-C_<13> segment was successfully achieved by VMAR, and 2) the stereoselective formation of C_6-C_7 double bond was accomplished by developing a unique E-olefin forming 8-membered RCM of silicon-tethered diene. Moreover, we observed a unique E-olefin forming 8-memberes ring RCM of silylene acetals, and proposed a plausible transition state as well as the structural requirement for E-olefin forming RCM. Although the E-olefin was produced only in a limited case, this methodology was quite useful for the total synthesis of TMC-151C (2).
• 自然が産み出す複雑さへの挑戦 : ビニグロールの全合成(A 化学系薬学)

  鈴木 孝洋  ファルマシア  46-  (7)  686  -687  2010/07/01  [Not refereed][Not invited]
  
• Zoanthamineの合成研究

  皆迫洋平, 山下大輔, 中崎敦夫, 鈴木孝洋, 小林進  日本薬学会年会要旨集  130th-  (2)  2010
• 抗腫瘍性環状リン脂質の硫黄誘導体(thia-cPA)の合成および生物活性評価

  田中遼, 加藤賢, 後藤真里, 野崎絵美, 花澤修和, 中崎敦夫, 鈴木孝洋, 室伏きみ子, 小林進  日本薬学会年会要旨集  130th-  (2)  2010
• ゾアンタミンアルカロイドの合成研究

  山下大輔, 皆迫洋平, 中島雄大, 中崎敦夫, 鈴木孝洋, 小林進  次世代を担う有機化学シンポジウム講演要旨集  8th-  2010
• ノルゾアンタミンのCDEFG環の構築 4位メチル基の環化への影響

  中島雄大, 山下大輔, 鈴木要, 中崎敦夫, 鈴木孝洋, 日景尚睦, 小林進  複素環化学討論会講演要旨集  40th-  2010
• PI-PLC特異的阻害物質(+)-Akaterpinの合成と構造決定

  細井勇人, 河井伸之, 萩原秀樹, 鈴木孝洋, 中崎敦夫, 小林進  有機合成シンポジウム講演要旨集  98th-  2010
• Claisen転位を基盤としたHistrionicotoxin類の合成研究

  齊藤洋平, 中崎敦夫, 鈴木孝洋, 小林進  日本薬学会年会要旨集  130th-  (2)  2010
• AngiomotinとAngiostatin及びRoxithromycinとの結合領域及び結合様式の解明

  高草木香織, 鈴木愛こ, 高草木洋一, 渡辺まどか, 松本勇記, 戸井崎絢, 鈴木孝洋, 中崎敦夫, 菅原二三男, 坂口謙吾  生化学  2010
• Exploration of Small-molecule-binding Proteins Using QCM-PD Method

  Toizaki Aya, Suzuki Aiko, Nakazaki Atsuo, Suzuki Takahiro, Takakusagi Yoichi, Sugawara Fumio, Sakaguchi Kengo, Kobayashi Susumu  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  36-  (0)  44  -44  2010  [Not refereed][Not invited]
   

  We attempted an identification of the molecular target of an antibiotic roxithromycin (RXM) using a T7 phage display (PD) screen on a quartz-crystal microbalance (QCM) device (QCM-PD). Wherein, we synthesized a RXM derivative that forms a self-assembled monolayer (SAM) for a specific RXM immobilization on the gold electrode surface of a QCM sensor chip. We then performed a one-cycle selection of RXM-binding peptides from a library of T7 phage-displayed peptides. As a result, we obtained 25 of RXM-recognizing sequences. Subsequent analysis utilizing the subset of sequence and receptor ligand contacts (RELIC) software clearly pinpointed several amino-acid residues within the RXM-binding site on the well-known direct targets, CYP3A4. Our findings demonstrate the effectiveness of this methodology and general applicability for a wide range of small-molecules. We are currently searching for another target responsible for anti-angiogenic effect of RXM.
• Synthetic Study of atropurpuran

  Sasaki Aya, Suzuki Takahiro, Kobayashi Susumu  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  36-  (0)  38  -38  2010  [Not refereed][Not invited]
   

  Atropurpuran was isolated from the roots of <I>Aconitum hemsleyanum var. atropurpureum</I> in 2009. Structurally, atropurpuran possesses an unprecedented skeleton, bis-bicyclo[2.2.2]octane, that includes a quaternary carbon shared with six six-membered rings.<BR>At the outset of our synthetic investigation on atropurpuran, we initially attempted to establish an efficient methodology for constructing a tetracyclic cage sketlon by employing an intramolecular reverse electron-demand Diels-Alder (REDDA) reaction. The preparation of REDDA precursor, having both MOB moiety and dienophile side chain, was achieved in 11 steps from guaiacol.<BR>The REDDA reaction of triene (in mesitylene, 180<SUP>o</SUP>C, 1 h) produced the desired cycloadduct in 77% yield. The structure of the cycloadduct was confirmed by NMR spectroscopy.
• T7ファージディスプレイ法を用いて同定したアンジオモチンとロキシスロマイシンの相互作用の検証

  鈴木愛こ, 高草木洋一, 渡辺まどか, 松本勇記, 戸井崎絢, 鈴木孝洋, 菅原二三男, 小林進, 坂口謙吾  日本分子生物学会年会講演要旨集  32nd-  (Vol.4)  2009
• Pseudodeflectusinの合成研究

  佐藤優奈, 野中美穂, 鈴木孝洋, 中崎敦夫, 小林進  日本薬学会関東支部大会講演要旨集  53rd-  2009
• TMC-151Cの全合成を目指したE選択的8員環形成閉環メタセシス反応の開発

  松井亮介, 瀬戸健太郎, 藤田和弘, 中崎敦夫, 鈴木孝洋, 小林進  有機合成シンポジウム講演要旨集  96th-  2009
• Synthesis and structure determination of PI-PLC specific inhibitor Akaterpin

  Hosoi Hayato, Kawai Nobuyuki, Hagiwara Hideki, Suzuki Takahiro, Nakazaki Atsuo, Kobayashi Susumu  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  35-  (0)  15  -15  2009  [Not refereed][Not invited]
   

  Akaterpin, a specific inhibitor of PI-specific PLC, consists of two decalin rings and a hydroquinone disulfate moiety. Relative stereochemistry of each decalin moiety was determined dependently, and, therefore, relative structure has not been yet determined. Our strategy to akaterpin was to construct the upper decalin first, and construct the lower dacalin by intramolecular Diels-Alder reaction. The resulting two isomers were separated, and each isomer was transformed to the target molecule. We found that the H-NMR spectrum of the target molecule (racemic) derived from the major isomer of Diels-Alder reaction was found to be identical to that of natural akaterpin. Thus, we were able to achieve a total synthesis of akaterpin (racemic) and determine the relative stereochemistry.
• 36 Asymmetric Total Synthesis of Antitumor Compound, (-)-FR182877(Oral Presentation)

  Tanaka Natsumi, Suzuki Takahiro, Matsumura Takehiko, Hosoya Yosuke, Nakada Masahisa  天然有機化合物討論会講演要旨集  (50)  239  -244  2008/09/01  [Not refereed][Not invited]
   

  (-)-FR182877 was isolated from the fermentation broth of Streptomyces sp. No. 9885 by a research group of Fujisawa Pharmaceutical Company in 1998. This compound possesses an unprecedented hexacyclic ring system containing a bridgehead double bond as part of a vinylogous carbonate unit and 12 stereogenic centers, and exhibits microtubule stabilizing activity similar to that of Taxol. Hence, the complex structure and promising bioactivity of (-)-FR182877 have attracted considerable attention from synthetic chemists. Our synthetic approach began with the conversion of known aldehyde 8 to precu...
• P-453 STUDIES ON ASYMMETRIC TOTAL SYNTHESIS OF (-)-FR182877

  Tanaka Natsumi, Suzuki Takahiro, Hosoya Yosuke, Nakada Masahisa  International Symposium on the Chemistry of Natural Products  2006-  "P  -453"  2006/07/23
• Synthetic studies on FR182877

  T Suzuki, T Matsumura, N Tanaka, M Nakada  ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY  229-  U514  -U514  2005/03  [Not refereed][Not invited]
  
• First total synthesis of antimitotic compound, (+)-phomopsidin

  T Suzuki, K Usui, Y Miyake, M Namikoshi, M Nakada  ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY  229-  U513  -U513  2005/03  [Not refereed][Not invited]
  
• 92(P-20) Synthetic Studies on Phomopsidin

  Suzuki Takahiro, Miyake Yoshiharu, Usui Kenji, Nakada Masahisa, Namikoshi Michio  天然有機化合物討論会講演要旨集  (45)  545  -550  2003/09/01  [Not refereed][Not invited]
   

  Phomopsidin was isolated from Phompsis sp. TUF95F47 by Namikoshi and co-workers in 1997, and its absolute structure and biological activity have been reported. Phomopsidin and its geometrical isomer (MK8383) showed potent inhibitory activity against assembly of microtubule proteins, exhibiting strong antitumor activity. It has been proposed that phomopsidin could be generated via the IMDA reaction of 1. Therefore, the potent antitumor activity and this biosynthetic background draw our attention to the synthesis of phomopsidin. We planned to synthesize the cis-decalin core 2 of phomopsidin f...
• Asymmetric Catalysis of Nozaki–Hiyama Allylation and Methallylaton with A New Tridentate Chiral Ligand

  Inoue Masahiro, Suzuki Takahiro, Nakada Masahisa  Proceedings of the Symposium on Progress in Organic Reactions and Syntheses  29-  (0)  210  -211  2003  [Not refereed][Not invited]
   

  We describe the development of a new tridentate chiral ligand effective for the asymmetric catalysis of Nozaki&mdash;Hiyama allylation, methallylation and propargylation. Various aldehydes (aromatic and aliphatic) were generally allylated or methallylated with good to excellent enantioselectivity (86-96% ee). The enantioselective reaction catalyzed by this Cr-ligand complex has great potential for natural product synthesis, and a key intermediate of calcitriol lactone synthesis was obtained with excellent diastereoselectivity (97% de, 91%). Another remarkable feature of this ligand is the stability of the Cr-ligand complex which was recovered after the enantioselective reaction and recycled without diminishing the enantioselectivity and yield.

Books etc

• 有機合成実験法ハンドブック第2版

  小林進, 鈴木孝洋 (Joint work16章 アルドール反応)
  丸善出版 2015/11
• 有機合成実験法ハンドブック 第2版

  鈴木孝洋 (Joint editor15 官能基の保護と脱保護)
  丸善出版 2015/11 (ISBN: 9784621089484) 1166 315-357

Presentations

• Synthetic Studies of Complex Natural Products by One-step Framework Construction Strategies  [Invited]

  Takahiro Suzuki

  11th Singapore International Chemistry Conference
• Biomimetic Total Syntheses of Chloropestolides, and Chloropupukeananin  [Invited]

  Takahiro Suzuki

  International Congress on Pure & Applied Chemistry (ICPAC) Kota Kinabalu 2022
• Total Synthesis of Complex Natural Products Based on Diels-Alder Reaction  [Invited]

  Takahiro Suzuki

  Keio International;Symposium on;Innovative;Synthesis of Complex Molecules  2019/12
• Total Syntheses of Complex Natural Products by Rapid Framework Construction Strategies  [Invited]

  Takahiro Suzuki

  Hokkaido mini-Symposium by Young Generations in Asia  2019/11
• Biomimetic Total Synthesis of Chloropupukeananin  [Invited]

  Takahiro Suzuki

  The 14th International Conference on Cutting-Edge Organic Chemistry in Asia  2019/09
• 新規香料化合物の創製に向けたジバレラン骨格の改良合成法の開発  [Not invited]

  岡本ゆきの, 和田善行, 村西修一, 鈴木孝洋, 谷野圭持

  The 62nd Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics  2018/10
• Total Synthesis of Atropurpuran  [Not invited]

  Takahiro Suzuki, Kenta Nakanishi, Takeshi Koyama, Susumu Kobayashi, Keiji Tanino

  22nd International Conference on Organic Synthesis (22-ICOS)  2018/09
• アトロプルプランの不斉全合成研究  [Not invited]

  古山岳史, 鈴木孝洋, 谷野圭持

  第53回天然物化学談話会  2018/07
• ヘチダン型ジテルペンの 収束的骨格構築法の開発  [Not invited]

  池田航, 鈴木孝洋, 谷野圭持

  第53回天然物化学談話会  2018/07
• ent-カウレンジテルペノイドKamebaninの全合成研究  [Not invited]

  菅野彩夏, 鈴木孝洋, 谷野圭持

  日本化学会第98春季年会  2018/03
• 3-ヒドロキシ-2-ピロンを用いた新規[4+3]付加環化反応の開発  [Not invited]

  柳澤尚宗, 鈴木孝洋, 谷野圭持

  日本化学会第98春季年会  2018/03
• 特異な構造の天然物の全合成と拡散的研究展開  [Invited]

  Takahiro Suzuki

  化学系学協会北海道支部2018年冬季研究発表会  2018/01
• Total Synthesis of Atropurpuran  [Not invited]

  Takahiro Suzuki

  59th Symposium on the Chemistry of Natural Products  2017/09
• 付加環化反応を基盤とした特異な環構造を有するテルペノイドの全合成研究  [Invited]

  Takahiro Suzuki

  The 61nd Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics  2017/09
• Enantioselective Total Synthesis of (+)-iso-A82775C  [Invited]

  Takahiro Suzuki

  International Symposium on Pure & Applied Chemistry (ISPAC) 2017  2017/06
• アトロプルプランの全合成  [Not invited]

  中西健太, 鈴木孝洋, 小林進, 谷野圭持

  日本化学会第97春季年会  2017/03
• iso-A82775Cの不斉全合成  [Not invited]

  渡邉壮一郎, 鈴木孝洋, 谷野圭持

  日本化学会第97春季年会  2017/03
• アイボレノイドAの全合成研究  [Not invited]

  堀口耕作, 鈴木孝洋, 谷野圭持

  The 60th Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics  2016/10
• 連続的環化反応を利用したent-カウレン類の合成研究  [Not invited]

  菅野彩夏, 鈴木孝洋, 谷野圭持

  The 60th Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics  2016/10
• Studies toward the Biomimetic Total Synthesis of Chloropupukeananin  [Invited]

  Takahiro Suzuki, Susumu Kobayashi, Keiji Tanino

  11th International Conference on Cutting-Edge Organic Chemistry in Asia  2016/10
• iso-A82775Cの全合成研究  [Not invited]

  渡邉壮一郎, 鈴木孝洋, 谷野圭持

  日本化学会北海道支部2016年夏季研究発表会  2016/07
• iso-A82775Cの全合成研究  [Not invited]

  渡邉壮一郎, 鈴木孝洋, 谷野圭持

  第51回天然物化学談話会  2016/07
• Synthesis and properties of novel Odorants containing Dibarrelane skeleton  [Not invited]

  和田善行, 鈴木孝洋, 吉田啓, 鈴木真也, 中西健太, 佐久間克也, 作田圭亮, 谷野圭持, 清水功雄

  Annual Meeting 2016 Sapporo of Japan Society for Bioscience, Biotechnology, and Agrochemistry  2016/03
• Construction of Cage-like Tricyclic Skeleton of Chloropupukeananin, an Inhibitor of HIV-1 Replication  [Invited]

  Takahiro Suzuki, Susumu Kobayashi, Keiji Tanino

  4th International Postgraduate Conference on Pharmaceutical Science  2016/02

Research Projects

• かご状飽和炭化水素合成のリビジット～一段階多環構築戦略による超効率的合成

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2024/04 -2028/03 

  Author : 鈴木 孝洋
• Innovative approach to illisimonin A by one-step multi-ring construction strategy

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)

  Date (from‐to) : 2020/04 -2023/03 

  Author : 鈴木 孝洋

   

  立体的に複雑な縮環構造（高次構造）を有する天然有機化合物（天然物）は、有用な生物活性を示すものが多く、医薬品・農薬として利用されてきた。それらの多くは有機化学的に合成されているが、依然として合成未達成のものも残されている。申請者の提案する「一段階多重環構築戦略」は、これらの合成困難な高次構造天然物に対する有効なアプローチであると考えている。そこで本研究では、近年シキミ属植物から単離が報告されたイリシモニンAを標的化合物とし、全合成を達成することで「一段階多重環構築戦略」の有用性を実証することにした。 昨年度に引き続き、イリシモニンAの骨格合成に向けてモデル化合物を用いた検討を行った。アロセドラン骨格からイリシモニンA骨格への骨格転位反応は、当初ベンジル酸転位による反応機構で進行すると推定していたが、詳細な反応条件の検討の結果、レトロクライゼン反応/アルドール反応の二段階の反応によって起きていることを明らかにした。これにより全合成達成には、ビシクロ[2.2.2]オクタン上の3つのケト基が必須であることが判明した。しかしながら、レトロクライゼン反応/アルドール反応によって生じるα-ヒドロキカルボン酸は望みでない立体化学の異性体が優先して得られているため、選択性の改善が今後の課題である。 現在イリシモニンAの全合成に向けて、すべての必要な官能基を備えた基質をもちいた合成に着手し、アロセドラン骨格の合成段階を検討している。
• Development and Application of Highly Stereoselective Aldol Reactions Using Chiral Amide

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)

  Date (from‐to) : 2010 -2012 

  Author : KOBAYASHI Susumu, SUZUKI Takahiro

   

  Diastereoselective reactions using chiral amide have extensively been utilized in the chiral synthesis of complex molecules in these decades.In this context, we have developed two types of diastereoselective aldol reactions. In the present investigation, we focused on (1) further improvement of vinylogous Mukaiyama aldol reaction, (2) general applicability of the stereocontrol of 1,2-diol including tertiary alcohol, and (3) application to biologically significant naturally occurring compounds.