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Synthetic Studies toward Large-scale production and Optimal Modification of Biologically Significant, Scarce Molecules

Research Project

Project/Area Number 25221301
Research Category

Grant-in-Aid for Scientific Research (S)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagoya University

Principal Investigator

Fukuyama Tohru  名古屋大学, 創薬科学研究科, 特任教授 (10272486)

Co-Investigator(Kenkyū-buntansha) 藤間 達哉  名古屋大学, 創薬科学研究科, 助教 (70733971)
下川 淳  名古屋大学, 創薬科学研究科, 助教 (60431889)
横島 聡  名古屋大学, 創薬科学研究科, 准教授 (10376593)
Project Period (FY) 2013-05-31 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥215,280,000 (Direct Cost: ¥165,600,000、Indirect Cost: ¥49,680,000)
Fiscal Year 2017: ¥43,940,000 (Direct Cost: ¥33,800,000、Indirect Cost: ¥10,140,000)
Fiscal Year 2016: ¥42,900,000 (Direct Cost: ¥33,000,000、Indirect Cost: ¥9,900,000)
Fiscal Year 2015: ¥44,460,000 (Direct Cost: ¥34,200,000、Indirect Cost: ¥10,260,000)
Fiscal Year 2014: ¥41,080,000 (Direct Cost: ¥31,600,000、Indirect Cost: ¥9,480,000)
Fiscal Year 2013: ¥42,900,000 (Direct Cost: ¥33,000,000、Indirect Cost: ¥9,900,000)
Keywords全合成 / 生体機能分子 / 量的供給 / 構造会へ念 / 天然有機化合物 / 構造改変
Outline of Final Research Achievements

There is an urgent need for the supply of reliable drugs for treatment of cancer and dementia in Japan. In this research, biologically important natural products are taken up in order to seek for a seed for drug development. The purpose is to establish a novel and robust synthetic pathway for total synthesis of natural products, which allows their structural modification to synthesize a more potent and selective drug candidate. Efficient synthetic pathways were successfully established and they were applied for preparation of the analogues.

Assessment Rating
Verification Result (Rating)

A-

Assessment Rating
Result (Rating)

A: Progress in the research is steadily towards the initial goal. Expected research results are expected.

Report

(10 results)
  • 2018 Research Progress Assessment (Verification Result) ( PDF )
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report   Abstract(Research Progress Assessment) ( PDF )   Research Progress Assessment (Result) ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Abstract ( PDF )   Annual Research Report
  • Research Products

    (53 results)

All 2017 2016 2015 2014 2013 Other

All Journal Article (24 results) (of which Peer Reviewed: 21 results,  Acknowledgement Compliant: 10 results,  Open Access: 1 results) Presentation (26 results) (of which Int'l Joint Research: 5 results) Remarks (3 results)

  • [Journal Article] Synthesis of Cardiopetaline via a Wagner-Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group2017

    • Author(s)
      Yoshitake Nishiyama, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 21 Pages: 5833-5835

    • DOI

      10.1021/acs.orglett.7b02812

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-lysergic acid2017

    • Author(s)
      Rentaro Kanno, Satoshi Yokoshima, Motomu Kanai, Tohru Fukuyama
    • Journal Title

      The Jornal of Antibiotics

      Volume: 71 Issue: 2 Pages: 240-247

    • DOI

      10.1038/ja.2017.80

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Huperzine Q2017

    • Author(s)
      Shun Tanimura, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 13 Pages: 3684-3686

    • DOI

      10.1021/acs.orglett.7b01633

    • NAID

      120006349132

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Morphine2017

    • Author(s)
      H. Umihara, S. Yokoshima, M. Inoue and T. Fukuyama
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 29 Pages: 6993-6995

    • DOI

      10.1002/chem.201701438

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total Synthesis of (-)-Tetrodotoxin and 11-norTTX-6(R)-ol2017

    • Author(s)
      Tomoaki Maehara, Keisuke Motoyama, Tatsuya Toma, Satoshi Yokoshima, and Tohru Fukuyama
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 6 Pages: 1549-1552

    • DOI

      10.1002/anie.201611574

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Lycopalhine A2017

    • Author(s)
      Yuji Ochi, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Synthesis

      Volume: 49 Issue: 01 Pages: 96-114

    • DOI

      10.1055/s-0036-1588878

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (-)-Gelsenicine, (-)-Gelsedine, (-)-Gelsedilam, (-)-14-Hydroxygelsenicine, and (-)-14,15-Dihydroxygelsenicine2016

    • Author(s)
      Takaaki Harada, Jun Shimokawa, Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 18 Pages: 4622-4625

    • DOI

      10.1021/acs.orglett.6b02263

    • NAID

      120005946825

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Cardiopetaline2016

    • Author(s)
      Yoshitake Nishiyama, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 10 Pages: 2359-2362

    • DOI

      10.1021/acs.orglett.6b00789

    • NAID

      120005866818

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a Divergent Synthetic Route to the Erythrina Alkaloids: Asymmetric Syntheses of 8-Oxo-erythrinine, Crystamidine, 8-Oxo-erythraline, and Erythraline2016

    • Author(s)
      Hirotatsu Umihara, Tomomi Yoshino, Jun Shimokawa, Masato Kitamura, Tohru Fukuyama
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 24 Pages: 6915-6918

    • DOI

      10.1002/anie.201602650

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Daphenylline2016

    • Author(s)
      Ryosuke Yamada, Yohei Adachi, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 20 Pages: 6067-6070

    • DOI

      10.1002/anie.201601958

    • NAID

      130007490838

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Conversion of Ester Moieties to 4-Bromophenyl Groups via Electrocyclic Reaction of Dibromocyclopropanes2015

    • Author(s)
      Kyosuke Ueda, Hirotatsu Umihara, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 13 Pages: 3191-3193

    • DOI

      10.1021/acs.orglett.5b01351

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight-Membered Cyclic Nitrone to Construct the 2-Azabicyclo[3.3.1]nonane Framework2015

    • Author(s)
      Takuya Higo,Tomoya Ukegawa, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 54 Issue: 25 Pages: 7367-7370

    • DOI

      10.1002/anie.201501633

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthetic Studies on Huperzine R: Construction of the 1-Azabicyclo[5.4.3]tetradec-6-ene Core2015

    • Author(s)
      Hiroshi Kumazaki, Rie Nakajima, Yuka Bessho, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Synlett

      Volume: 26 Issue: 15 Pages: 2131-2134

    • DOI

      10.1055/s-0034-1380425

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis of the Common Core Structure of the Stemofoline Alkaloids2015

    • Author(s)
      Eiji Ideue, Jun Shimokawa, Tohru Fukuyama
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 20 Pages: 4964-4967

    • DOI

      10.1021/acs.orglett.5b02373

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (-)-Oxycodone2014

    • Author(s)
      Atsushi Kimishima, Hirotatsu Umihara, Akihiro Mizoguchi, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 23 Pages: 6244-6247

    • DOI

      10.1021/ol503175n

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A Unified Strategy for Kainoid Synthesis2014

    • Author(s)
      Masaya Fujii, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Europian Journal of Organic Chemistry

      Volume: 2014 Issue: 22 Pages: 4823-4836

    • DOI

      10.1002/ejoc.201402452

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total Synthesis of (-)-Lepistine2014

    • Author(s)
      Yusuke Kitabayashi, Satoshi Yokoshima and Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 11 Pages: 2862-2864

    • DOI

      10.1021/ol5010033

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] New photocleavable linker: α-thioacetophenone-type linker2014

    • Author(s)
      Hirotaka Yonezawa, Yoshitake Nishiyama, Koji Takeo, Takeshi Iwatsubo, Taisuke Tomita, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 24 Issue: 13 Pages: 2831-2833

    • DOI

      10.1016/j.bmcl.2014.04.104

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total Synthesis of (-)-Lepenine2014

    • Author(s)
      Yoshitake Nishiyama, Yuki Han-ya, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 18 Pages: 6598-6601

    • DOI

      10.1021/ja503023h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a route to chiral epidithiodioxopiperazine moieties and application to the asymmetric synthesis of (+)-hyalodendrin2014

    • Author(s)
      Ren Takeuchi, Jun Shimokawa and Tohru Fukuyama
    • Journal Title

      Chemical Science

      Volume: 5 Issue: 5 Pages: 2003-2006

    • DOI

      10.1039/c3sc53222d

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of spirotryprostatin A2014

    • Author(s)
      Katsushi Kitahara, Jun Shimokawa and Tohru Fukuyama
    • Journal Title

      Chemical Science

      Volume: 5 Issue: 3 Pages: 904-907

    • DOI

      10.1039/c3sc52525b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] TMSCN/DBU-Mediated Facile Redox Transformation of α,β-Unsaturated Aldehydes to Carboxylic Acid Derivatives2014

    • Author(s)
      Hiromi Kaise, Jun Shimokawa and Tohru Fukuyama
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 3 Pages: 727-729

    • DOI

      10.1021/ol403415z

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of ecteinascidin 7432013

    • Author(s)
      Fumiki Kawagishi, Tomohikko Inui, Tatsuya Toma, Satoshi Yokoshima, Tohru Fukuyama
    • Journal Title

      Journal of the American chemical society

      Volume: 135 Issue: 37 Pages: 13684-13687

    • DOI

      10.1021/ja408034x

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Lysergic Acid2013

    • Author(s)
      Satoshi Umezaki, Satoshi Yokoshima and Tohru Fukuyama
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 16 Pages: 4230-4233

    • DOI

      10.1021/ol4019562

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] リコポセラミンRの合成研究2017

    • Author(s)
      渡邊 慎也・石川 雅嗣・野村 俊宗・福山 透・横島 聡
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部 合同学術大会2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthetic Studies on Ecteinascidin 7432017

    • Author(s)
      吉田瑛二・中島長安・藤間達哉・福山 透・横島 聡
    • Organizer
      第9回集積型有機合成国際シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Huperzine Rの合成研究2017

    • Author(s)
      野村 俊宗・福山 透・横島 聡
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] モルヒネの合成研究2017

    • Author(s)
      林 尚毅・角川 仁規・藤間 達哉・福山 透・横島 聡
    • Organizer
      第35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Total synthesis of Daphenylline2016

    • Author(s)
      Ryosuke Yamada, Yohei Adachi, Yokoshima Satoshi, Tohru Fukuyama
    • Organizer
      21st International Conference on Organic Synthesis
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] (-)-テトロドトキシンの全合成2016

    • Author(s)
      前原 知明, 本山 敬祐, 藤間 達哉, 横島 聡, 福山 透
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Related Report
      2016 Annual Research Report
  • [Presentation] Huperzine Rの合成研究2016

    • Author(s)
      野村 俊宗、横島 聡、福山 透
    • Organizer
      第110回有機合成シンポジウム
    • Related Report
      2016 Annual Research Report
  • [Presentation] (-)-テトロドトキシンの全合成2016

    • Author(s)
      前原 知明・本山 敬祐・藤間 達哉・横島 聡・福山 透
    • Organizer
      第47回 中部化学関係学協会支部連合秋季大会
    • Related Report
      2016 Annual Research Report
  • [Presentation] (-)-テトロドトキシンの全合成2016

    • Author(s)
      前原 知明・本山 敬祐・藤間 達哉・横島 聡・福山 透
    • Organizer
      第58回天然有機化合物討論会
    • Related Report
      2016 Annual Research Report
  • [Presentation] Total synthesis of Huperzine R2016

    • Author(s)
      Toshimune Nomura, Yokoshima Satoshi, Tohru Fukuyama
    • Organizer
      15th Belgian Organic Synthesis Symposium
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Total Synthesis of Lepistine2015

    • Author(s)
      Yusuke Kitabayashi, Satoshi Yokoshima, Tohru Fukuyama
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      アメリカ
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic studies on ecteinascidin 7432015

    • Author(s)
      Eiji Yoshida, Tatsuya Toma, Satoshi Yokoshima, Tohru Fukuyama
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      アメリカ
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] エクテナサイジン743の合成研究2015

    • Author(s)
      吉田 瑛二, 藤間 達哉, 横島 聡, 福山 透
    • Organizer
      第46回 中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      三重
    • Year and Date
      2015-11-07
    • Related Report
      2015 Annual Research Report
  • [Presentation] ダフェニリンの全合成2015

    • Author(s)
      山田 諒介, 安達 庸平, 横島 聡, 福山 透
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      横浜
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic Studies on (-)-Tetrodotoxin2015

    • Author(s)
      Tomoaki Maehara, Keisuke Motoyama, Tatsuya Toma, Satoshi Yokoshima, Tohru Fukuyama
    • Organizer
      24th International Symposium; Synthesis in Organic Chemistry
    • Place of Presentation
      イギリス
    • Year and Date
      2015-07-20
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] エステルおよびその類縁体を基質とした新規ベンゼン環構築法の開発2015

    • Author(s)
      上田 喬介、海原 浩辰、横島 聡、福山 透
    • Organizer
      第13回次世代を担う有機化学シンポジウム
    • Place of Presentation
      草津
    • Year and Date
      2015-05-22
    • Related Report
      2015 Annual Research Report
  • [Presentation] オキシコドンの合成研究2014

    • Author(s)
      海原浩辰、君嶋 敦、溝口明祐、横島 聡、福山 透
    • Organizer
      第40回 反応と合成のシンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] カイノイドの効率的かつ網羅的な合成法の開発2014

    • Author(s)
      藤井正哉、横島 聡、福山 透
    • Organizer
      第106回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-11-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] 特異な構造を有するリコポジウムアルカロイドの合成研究2014

    • Author(s)
      横島 聡、谷村 瞬、熊崎太信、福山 透
    • Organizer
      第56回 天然有機化合物討論会
    • Place of Presentation
      高知
    • Year and Date
      2014-10-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] (-)-レペニンの全合成2014

    • Author(s)
      西山義剛、半矢祐己、横島 聡、福山 透
    • Organizer
      第44回 複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] レピスチンの全合成2014

    • Author(s)
      北林祐介、横島 聡、福山 透
    • Organizer
      第12回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-05-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Haliclonin Aの合成研究2013

    • Author(s)
      河岸文希、横島 聡、福山 透
    • Organizer
      第104回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2013-11-06 – 2013-11-07
    • Related Report
      2013 Annual Research Report
  • [Presentation] サラインAの合成研究2013

    • Author(s)
      肥後拓也、請川智哉、横島 聡、福山 透
    • Organizer
      第39回 反応と合成の進歩シンポジウム
    • Place of Presentation
      博多
    • Year and Date
      2013-11-05 – 2013-11-06
    • Related Report
      2013 Annual Research Report
  • [Presentation] Total Synthesis of (±)-Lepenine2013

    • Author(s)
      Yoshitake Nishiyama, Yuki Han-ya, Satoshi Yokoshima, Tohru Fukuyama
    • Organizer
      13th International Conference on the Chemistry of Antibiotics and other bioactive compounds
    • Place of Presentation
      山梨
    • Year and Date
      2013-10-24 – 2013-10-27
    • Related Report
      2013 Annual Research Report
  • [Presentation] (+)-Roseophilinの合成研究2013

    • Author(s)
      岩井ゆり、中島 彩、下川 淳、福山 透
    • Organizer
      第43回 複素環化学討論会
    • Place of Presentation
      岐阜
    • Year and Date
      2013-10-17 – 2013-10-19
    • Related Report
      2013 Annual Research Report
  • [Presentation] エリスリナアルカロイドの合成研究2013

    • Author(s)
      海原浩辰、吉野友美、下川 淳、北村雅人、福山 透
    • Organizer
      第55回 天然有機化合物討論会
    • Place of Presentation
      京都
    • Year and Date
      2013-09-18 – 2013-09-20
    • Related Report
      2013 Annual Research Report
  • [Remarks] 天然物化学分野研究室

    • URL

      http://www.ps.nagoya-u.ac.jp/lab_pages/natural_products/index.html

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
  • [Remarks] 名古屋大学大学院創薬科学研究科 天然物化学分野

    • URL

      http://www.ps.nagoya-u.ac.jp/lab_pages/natural_products/index.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 名古屋大学大学院創薬化学研究科 天然物化学分野

    • URL

      http://www.ps.nagoya-u.ac.jp/lab_pages/natural_products/index.html

    • Related Report
      2014 Annual Research Report

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Published: 2013-06-20   Modified: 2019-05-15  

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