2018年01月, 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
鈴木孝洋

2016年10月, Asian Core Program Lectureship Award from HongKong　　　　　　　　　　　　　　　
鈴木孝洋, 国際学会・会議・シンポジウム等の賞

2016年10月, Asian Core Program Lectureship Award from China　　　　　　　　　　　　　　　
鈴木孝洋, 国際学会・会議・シンポジウム等の賞

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年08月19日
研究論文（学術雑誌）

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, 2024年06月10日
英語, 研究論文（学術雑誌）, 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
鈴木孝洋
有機合成化学協会誌, 82, 4, 2024年04月01日
英語, 研究論文（学術雑誌）

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年03月
研究論文（学術雑誌）

Synthesis of dihydrotropone derivatives using an anionic 8π-electrocyclic reaction
Ranmaru Kato, Takahiro Suzuki, Keiji Tanino
Chemical Communications, 2024年
研究論文（学術雑誌）

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年
研究論文（学術雑誌）

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年01月18日, ［国際誌］
英語, 研究論文（学術雑誌）, 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
American Chemical Society (ACS), 2022年12月28日
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, Georg Thieme Verlag KG, 2022年12月27日
研究論文（学術雑誌）, 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, Wiley, 2022年12月18日
研究論文（学術雑誌）

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年11月04日
研究論文（学術雑誌）

Total Syntheses of Chloropupukeananin and Its Related Natural Products
Takahiro Suzuki
Organics, 2022年09月09日
研究論文（学術雑誌）

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}), 2022年09月09日, ［査読有り］
英語, 研究論文（学術雑誌）

Total Syntheses of Chloropupukeananin and Its Related Natural Products
Takahiro Suzuki
Organics, 2022年09月
研究論文（学術雑誌）

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), 2022年07月22日
研究論文（学術雑誌）

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, American Chemical Society ({ACS}), 2021年12月17日, ［査読有り］
英語, 研究論文（学術雑誌）

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, Georg Thieme Verlag KG, 2021年11月16日
研究論文（学術雑誌）, 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, American Chemical Society (ACS), 2021年11月11日
研究論文（学術雑誌）

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, American Chemical Society ({ACS}), 2021年11月05日
研究論文（学術雑誌）

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, Georg Thieme Verlag {KG}, 2021年10月29日
英語, 研究論文（学術雑誌）,
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, American Chemical Society (ACS), 2021年10月29日
研究論文（学術雑誌）

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, 2021年09月02日
研究論文（学術雑誌）, 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, American Chemical Society ({ACS}), 2020年08月07日
研究論文（学術雑誌）

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, The Japan Institute of Heterocyclic Chemistry, 2019年, ［査読有り］, ［招待有り］
英語, 研究論文（学術雑誌）

Asymmetric Total Synthesis of (−)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family
Takahiro Suzuki, Soichiro Watanabe, Muhammet Uyanik, Kazuaki Ishihara, Susumu Kobayashi, Keiji Tanino
Organic Letters, 20, 13, 3919, 3922, American Chemical Society ({ACS}), 2018年07月06日, ［査読有り］
英語, 研究論文（学術雑誌）

天然物化学はおもしろい!Iso‐A82775Cの不斉全合成
鈴木孝洋
有機合成化学協会誌, 76, 5, 462, 465, Society of Synthetic Organic Chemistry, 2018年, ［査読有り］, ［招待有り］
日本語, 研究論文（学術雑誌）, (+)-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 <i>anti</i>-selective Cu-mediated S_N2' reaction to afford the axially chiral vinylallene moiety. Herein the details and inside stories are disclosed.</p>

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, PERGAMON-ELSEVIER SCIENCE LTD, 2017年06月, ［査読有り］, ［招待有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2017年02月, ［査読有り］
英語, 研究論文（学術雑誌）, (+)-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, AMER CHEMICAL SOC, 2016年02月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2015年03月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2015年01月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER, 2015年01月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2014年03月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, 50, 2013年12月18日, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PHARMACEUTICAL SOC JAPAN, 2013年05月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2013年04月, ［査読有り］
英語, 研究論文（学術雑誌）, 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.

ジアゾ基を有する天然物, Kinamycin 類および Lomaiviticin 類の合成研究
鈴木 孝洋
有機合成化学協会誌, 70, 10, 1069, 1070, 社団法人 有機合成化学協会, 2012年10月01日, ［査読有り］, ［招待有り］
日本語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2012年09月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2012年05月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PHARMACEUTICAL SOC JAPAN, 2012年01月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, WILEY-V C H VERLAG GMBH, 2012年, ［査読有り］
英語, 研究論文（学術雑誌）

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, PERGAMON-ELSEVIER SCIENCE LTD, 2011年09月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2011年07月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2011年06月, ［査読有り］
英語, 研究論文（学術雑誌）, 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.

(-)-FR182877の不斉全合成
鈴木(田中) 奈津美, 鈴木 孝洋, 松村 岳彦, 細谷 洋介, 中里 知幸, 中田 雅久
Journal of Synthetic Organic Chemistry Japan, 69, 6, 646, 660, SOC SYNTHETIC ORGANIC CHEM JPN, 2011年06月, ［査読有り］
日本語, 研究論文（学術雑誌）, 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 α-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogen...

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, PHARMACEUTICAL SOC JAPAN, 2011年04月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2011年02月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, WILEY-BLACKWELL, 2011年02月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2011年01月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, WILEY-BLACKWELL, 2011年, ［査読有り］
英語, 研究論文（学術雑誌）

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, WILEY-BLACKWELL, 2011年, ［査読有り］
英語, 研究論文（学術雑誌）

Concise Approach to Pupukeanane Skeleton: Synthetic Study of Chloropupukeananin
Takahiro Suzuki, Susumu Kobayashi
ORGANIC LETTERS, 12, 13, 2920, 2923, AMER CHEMICAL SOC, 2010年07月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2010年04月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, WILEY-BLACKWELL, 2010年, ［査読有り］
英語, 研究論文（学術雑誌）

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, PERGAMON-ELSEVIER SCIENCE LTD, 2009年09月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, WILEY-V C H VERLAG GMBH, 2009年, ［査読有り］
英語, 研究論文（学術雑誌）

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, WILEY-V C H VERLAG GMBH, 2009年, ［査読有り］
英語, 研究論文（学術雑誌）

Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction
Nobuyuki Hayashi, Takahiro Suzuki, Kenji Usui, Masahisa Nakada
TETRAHEDRON, 65, 4, 888, 895, PERGAMON-ELSEVIER SCIENCE LTD, 2009年01月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2008年06月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, JOHN WILEY & SONS INC, 2008年, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2007年09月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2007年09月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, PERGAMON-ELSEVIER SCIENCE LTD, 2006年03月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2004年02月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, GEORG THIEME VERLAG KG, 2003年03月, ［査読有り］
英語, 研究論文（学術雑誌）, 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, AMER CHEMICAL SOC, 2003年02月, ［査読有り］
英語, 研究論文（学術雑誌）

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, PERGAMON-ELSEVIER SCIENCE LTD, 2002年04月, ［査読有り］
英語, 研究論文（学術雑誌）, 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.

(+)-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年

ピリダジンを用いた連続的分子内Diels-Alder反応による新規ビシクロ[2.2.2]オクタン構築法の開発
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年

アトロプルプランの改良合成法研究
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年

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年

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年

アトロプルプランの全合成
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年

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年

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年

DNAポリメラーゼYファミリー阻害剤ペニシリオール類の合成研究
遠藤正伍, 黒澤敦, 志村聡美, 竹内倫文, 鈴木孝洋, 紙透伸治, 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年

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年

抗ウイルス活性を有する新規環状デプシペプチドMA026の全合成と標的分子の探索
志村 聡美, 石間 正浩, 太田 育恵, 筒井 悦子, 紙透 伸治, 村田 寛, 山崎 隆之, 鈴木 孝洋, 倉持 幸司, 竹内 倫文, 小林 進, 菅原 二三男, 天然有機化合物討論会講演要旨集, 55, 0, 2013年
<p>【 背景 】</p><p>水産養殖の現場では、魚類病原ウイルスによる感染症の発生が水産資源の安定供給に深刻な影響を及ぼす。サケ科魚類の伝染性造血器壊死症ウイルス(Infectious hematopoietic necrosis virus : IHNV) はニジマス養殖に甚大な被害をもたらすが、同じ養殖池の中でもIHNVに耐性を示す個体と耐性を示さない個体がいた。両者の違いを調べると、前者では特定の細菌が消化管に生息していた。この細菌が生産し、抗ウイルス活性を示す物質としてMA026 (1) が単離された¹⁾。MA026は当研究室で単離、構造決定された新規環状デプシペプチドであり、アミノ酸14残基からなる鎖環デプシペプチドに脂肪酸が結合した複雑な構造を有する (Figure 1)。本化合物はIHNVだけでなく、エンベロープを有する複数種のウイルスの増殖を抑制するが、その作用機序は解明されていない。本研究は、MA026の効率的な化学合成法の確立と標的分子の同定を目的とした。</p><p>【 合成戦略 】 </p><p>MA026はアミノ酸8残基からなるマクロラクトン構造に、アミノ酸6残基からなる鎖状ペプチド、N末端に (R)-3-ヒドロキシデカノイル基が結合した構造を有する。我々は、MA026を2つのセグメント2, 3に分割し、それぞれ合成した後縮合し、収束的に合成する計画を立案した (Scheme 1)。環状デプシペプチド3の合成では、アミド化に比べて反応性の低いエステル化を合成の早い段階で行うこととし、ペプチド主鎖の分岐構造を有する2つの環化基質4, 5を設定した。また、4と5は共通中間体ヘキサデプシペプチド6から導くこととした。6にテトラペプチドを縮合し、2行程で4 を合成したが、4の環化は進行しなかった²⁾。4の環化部位はD-Leu¹³-D-Val¹⁴であるが、2つの反応点の分岐からの距離が大きく異なるため、分子内マクロラクタム化が進行するにはより大きなコンフォメーション変化が必要になると予想された。一方、環化部位がD-Gln¹¹-L-Leu¹²となる5では、2つの反応点の分岐からの距離はほぼ同じであり、4よりも環化しやすいと考えた。よって、3はデカデプシペプチド5の分子内マクロラクタム化により導くこととした。</p><p>【 デカデプシペプチド5の合成 】</p><p> </p><p>Alloc-L-Gln-OH (7) を出発原料とし、5行程でジペプチド9を合成した (Scheme 2)。また、MA026を構成する保護アミノ酸を調製し、それらを縮合し、脱保護することでジペプチド10、11、12、13を得た。次に9と10を縮合し、テトラペプチド14を得た (Scheme 3)。14のD-Ser側鎖ヒドロキシ基と11をエステル縮合することでヘキサデプシペプチド6 を合成した。6の有機溶媒に対する溶解性は高いが、ペプチド鎖の伸長と伴に溶解性の減少が観察された。ペプチドの溶解性を維持するためBCBを用いて6のTr基は除去せずBoc基を選択的に除去し、アミンとした。得られたアミンと12を縮合し、オクタデプシペプチド15を得た。次に15のBn基の脱保護を検討した。ジペプチド9の合成では (Scheme 2) THF溶媒中、Pd/Cを触媒とした加水素分解反応によりBn基のみを除去し、目的のカルボン酸を98%の収率で得ることができた。一方、15はTHFのような非プロトン性溶媒に難溶であり、MeOHを溶媒として加水素分解を行ったとこ</p><p>(View PDFfor the rest of the abstract.)</p>, 天然有機化合物討論会実行委員会, 日本語

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年
上原記念生命科学財団, 日本語

P-25 抗菌活性物質ピロシジンBの合成研究(ポスター発表の部)
田中 遼, 大石 健太郎, 高梨 憲幸, 長野 智彦, 水津 拓, 鈴木 孝洋, 小林 進, 天然有機化合物討論会講演要旨集, 54, 339, 344, 2012年09月01日
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., 天然有機化合物討論会, 日本語

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年08月
GEORG THIEME VERLAG KG, 英語, 研究発表ペーパー・要旨（国際会議）

P-8 アトロプルプランの合成研究(ポスター発表の部)
鈴木 孝洋, 佐々木 綾, 小林 進, 天然有機化合物討論会講演要旨集, 53, 505, 510, 2011年09月02日
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., 天然有機化合物討論会, 日本語

P-62 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(ポスター発表の部)
志村 聡美, 石間 正浩, 太田 育恵, 筒井 悦子, 紙透 伸治, 村田 寛, 山崎 隆之, 鈴木 孝洋, 倉持 幸司, 竹内 倫文, 小林 進, 菅原 二三男, 天然有機化合物討論会講演要旨集, 53, 667, 672, 2011年09月02日
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., 天然有機化合物討論会, 日本語

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年04月28日
日本語

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年

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年

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年
英語, 研究発表ペーパー・要旨（全国大会，その他学術会議）

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 発表要旨概要, 37, 0, 77, 77, 2011年
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., 日本薬学会化学系薬学部会, 日本語

chloropupukeananinの合成研究
鈴木 孝洋, 宮嶋 ゆりあ, 鈴木 要, 小清水 正樹, 小林 進, 反応と合成の進歩シンポジウム 発表要旨概要, 37, 0, 51, 51, 2011年
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., 日本薬学会化学系薬学部会, 日本語

3 ビニロガス向山アルドール反応と閉環メタセシスを鍵反応とした抗腫瘍性物質(+)-TMC-151Cの全合成(口頭発表の部)
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, 天然有機化合物討論会講演要旨集, 52, 13, 18, 2010年09月01日
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)., 天然有機化合物討論会, 日本語

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年07月01日
公益社団法人日本薬学会, 日本語

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年

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年

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年

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年

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年

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年

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年

QCM-PD法を用いた医薬小分子の標的タンパク質の特定
戸井崎 絢, 鈴木 愛こ, 中崎 敦夫, 鈴木 孝洋, 高草木 洋一, 菅原 二三男, 坂口 謙吾, 小林 進, 反応と合成の進歩シンポジウム 発表要旨概要, 36, 0, 44, 44, 2010年
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., 日本薬学会化学系薬学部会, 日本語

特異なかご状骨格を有するatropurpuranの合成研究
佐々木 綾, 鈴木 孝洋, 小林 進, 反応と合成の進歩シンポジウム 発表要旨概要, 36, 0, 38, 38, 2010年
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., 日本薬学会化学系薬学部会, 日本語

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年

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年

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年

PI-PLC特異的阻害物質アカテルピンの合成と構造決定
細井 勇人, 河井 伸之, 萩原 秀樹, 鈴木 孝洋, 中崎 敦夫, 小林 進, 反応と合成の進歩シンポジウム 発表要旨概要, 35, 0, 15, 15, 2009年
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., 日本薬学会化学系薬学部会, 日本語

36 抗腫瘍性化合物(-)-FR182877の不斉全合成(口頭発表の部)
田中 奈津美, 鈴木 孝洋, 松村 岳彦, 細谷 洋介, 中田 雅久, 天然有機化合物討論会講演要旨集, 50, 239, 244, 2008年09月01日
(-)-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..., 天然有機化合物討論会, 日本語

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年07月23日
天然有機化合物討論会, 英語

Synthetic studies on FR182877
T Suzuki, T Matsumura, N Tanaka, M Nakada, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 229, U514, U514, 2005年03月
AMER CHEMICAL SOC, 英語, 研究発表ペーパー・要旨（国際会議）

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年03月
AMER CHEMICAL SOC, 英語, 研究発表ペーパー・要旨（国際会議）

92(P-20) 抗腫瘍性抗生物質phomopsidinの全合成研究(ポスター発表の部)
鈴木 孝洋, 三宅 祥元, 臼井 研二, 中田 雅久, 浪越 通夫, 天然有機化合物討論会講演要旨集, 45, 545, 550, 2003年09月01日
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..., 天然有機化合物討論会, 日本語

新規光学活性三座配位子を用いた触媒的不斉野崎–檜山アリル化反応
井上 雅大, 鈴木 孝洋, 中田 雅久, 反応と合成の進歩シンポジウム 発表要旨概要, 29, 0, 210, 211, 2003年
二価のクロム塩を用いた炭素&ndash;炭素結合形成反応（野崎&ndash;檜山反応）は、その高い官能基選択性、立体選択性から非常に有用であり、多くの天然物の全合成に適用されてきた。しかし、野崎&ndash;檜山反応の不斉触媒化の報告例は少なく、そのエナンチオ選択性も満足いくものではなかった。そこで我々は新規の不斉配位子をデザイン、合成し、触媒的不斉野崎&ndash;檜山アリル化反応を検討した。¹⁾カルバゾールを原料とし５行程で不斉配位子の合成に成功した。この配位子を用いて野崎&ndash;檜山アリル化反応をおこなったところ、アルデヒドの種類によらず高エナンチオ選択にホモアリルアルコールを得ることに成功した（86&ndash;95% ee）。²⁾またメタリル化についても一般性が見られた(90&ndash;96% ee)。興味深いことに、このクロムと不斉配位子との錯体は空気や水に対して安定であり、繰り返し触媒反応を行うことが可能であった。その際、生成物のエナンチオ選択性に低下は見られなかった。さらに、本反応の天然物合成への適用例も併せて報告する。, 日本薬学会化学系薬学部会

有機合成実験法ハンドブック第2版　　　　　　　　　　　　　　　
小林進, 鈴木孝洋, 16章 アルドール反応
丸善出版, 2015年11月, ［共著］

有機合成実験法ハンドブック 第2版　　　　　　　　　　　　　　　
鈴木孝洋, 15 官能基の保護と脱保護
丸善出版, 2015年11月, 9784621089484, 1166, 315-357, 日本語, 学術書, ［共編者(共編著者)］

Synthetic Studies of Complex Natural Products by One-step Framework Construction Strategies
Takahiro Suzuki
11th Singapore International Chemistry Conference, 英語, 口頭発表（招待・特別）
2022年12月11日 - 2022年12月14日, 33431038, ［招待講演］

Biomimetic Total Syntheses of Chloropestolides, and Chloropupukeananin
Takahiro Suzuki
International Congress on Pure & Applied Chemistry (ICPAC) Kota Kinabalu 2022, 英語, 口頭発表（招待・特別）
2022年11月22日 - 2022年11月27日, 33431038, ［招待講演］

Total Synthesis of Complex Natural Products Based on Diels-Alder Reaction
Takahiro Suzuki
Keio International;Symposium on;Innovative;Synthesis of Complex Molecules, 2019年12月14日, 英語, 口頭発表（招待・特別）
33431038, ［招待講演］

Total Syntheses of Complex Natural Products by Rapid Framework Construction Strategies
Takahiro Suzuki
Hokkaido mini-Symposium by Young Generations in Asia, 2019年11月15日, 英語, 口頭発表（招待・特別）
33431038, ［招待講演］

Biomimetic Total Synthesis of Chloropupukeananin
Takahiro Suzuki
The 14th International Conference on Cutting-Edge Organic Chemistry in Asia, 2019年09月28日, 英語, ポスター発表
33431038, ［招待講演］

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　　　　　　　　　　　　　　　
岡本ゆきの, 和田善行, 村西修一, 鈴木孝洋, 谷野圭持
第62回香料・テルペンおよび精油化学, 2018年10月14日, 日本語, 口頭発表（一般）
［国内会議］

Total Synthesis of Atropurpuran　　　　　　　　　　　　　　　
鈴木孝洋, 中西健太, 古山岳史, 小林進, 谷野圭持
22nd International Conference on Organic Synthesis (22-ICOS), 2018年09月17日, 英語, 口頭発表（一般）
［国際会議］

アトロプルプランの不斉全合成研究　　　　　　　　　　　　　　　
古山岳史, 鈴木孝洋, 谷野圭持
第53回天然物化学談話会, 2018年07月05日, 日本語, ポスター発表
［国内会議］

ヘチダン型ジテルペンの 収束的骨格構築法の開発　　　　　　　　　　　　　　　
池田航, 鈴木孝洋, 谷野圭持
第53回天然物化学談話会, 2018年07月04日, 日本語, ポスター発表
［国内会議］

ent-カウレンジテルペノイドKamebaninの全合成研究　　　　　　　　　　　　　　　
菅野彩夏, 鈴木孝洋, 谷野圭持
日本化学会第98春季年会, 2018年03月23日, 日本語, 口頭発表（一般）
［国内会議］

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　　　　　　　　　　　　　　　
柳澤尚宗, 鈴木孝洋, 谷野圭持
日本化学会第98春季年会, 2018年03月22日, 日本語, 口頭発表（一般）
［国内会議］

特異な構造の天然物の全合成と拡散的研究展開　　　　　　　　　　　　　　　
鈴木孝洋
化学系学協会北海道支部2018年冬季研究発表会, 2018年01月17日, 日本語, 口頭発表（招待・特別）
［招待講演］, ［国内会議］

アトロプルプランの全合成　　　　　　　　　　　　　　　
鈴木孝洋
第 59 回天然有機化合物討論会, 2017年09月20日, 日本語, 口頭発表（一般）
［国内会議］

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
第61回香料・テルペンおよび精油化学, 2017年09月09日, 日本語, 口頭発表（招待・特別）
［招待講演］, ［国内会議］

Enantioselective Total Synthesis of (+)-iso-A82775C　　　　　　　　　　　　　　　
鈴木孝洋
International Symposium on Pure & Applied Chemistry (ISPAC) 2017, 2017年06月10日, 英語, 口頭発表（招待・特別）
［招待講演］, ［国際会議］

アトロプルプランの全合成　　　　　　　　　　　　　　　
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年03月18日, 日本語, 口頭発表（一般）
［国内会議］

iso-A82775Cの不斉全合成　　　　　　　　　　　　　　　
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年03月18日, 日本語, 口頭発表（一般）
［国内会議］

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
第60回香料・テルペンおよび精油化学, 2016年10月30日, 日本語, 口頭発表（一般）
［国内会議］

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
第60回香料・テルペンおよび精油化学, 2016年10月30日, 日本語, 口頭発表（一般）
［国内会議］

Studies toward the Biomimetic Total Synthesis of Chloropupukeananin　　　　　　　　　　　　　　　
Takahiro Suzuki, Susumu Kobayashi, Keiji Tanino
11th International Conference on Cutting-Edge Organic Chemistry in Asia, 2016年10月29日, 英語, ポスター発表
［招待講演］, ［国際会議］

iso-A82775Cの全合成研究　　　　　　　　　　　　　　　
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年07月23日, 日本語, 口頭発表（一般）
［国内会議］

iso-A82775Cの全合成研究　　　　　　　　　　　　　　　
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年07月07日, 日本語, ポスター発表
［国内会議］

ジバレラン骨格を有する新規香料化合物の創製とその香気特性　　　　　　　　　　　　　　　
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
日本農芸化学会2016年度大会, 2016年03月28日, 日本語, ポスター発表
［国内会議］

Construction of Cage-like Tricyclic Skeleton of Chloropupukeananin, an Inhibitor of HIV-1 Replication　　　　　　　　　　　　　　　
Takahiro Suzuki, Susumu Kobayashi, Keiji Tanino
4th International Postgraduate Conference on Pharmaceutical Science, 2016年02月27日, 英語, 口頭発表（招待・特別）
［招待講演］, ［国際会議］