• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Synthetic studies of polyfunctionalized natural products with highly-fused ring systems

Research Project

Project/Area Number 26713001
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Chemical pharmacy
Research InstitutionNagoya University

Principal Investigator

Satoshi Yokoshima  名古屋大学, 創薬科学研究科, 教授 (10376593)

Research Collaborator KITABAYASHI Yusuke  
YAMADA Ryosuke  
OCHI Yuji  
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000)
Fiscal Year 2016: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2015: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2014: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Keywordsアルカロイド / 天然物 / 全合成 / 複素環 / 環化付加反応 / 天然有機化合物 / 医薬品 / 縮環構造 / 多官能性
Outline of Final Research Achievements

Synthetic studies of polyfunctionalized natural products with highly-fused ring systems were conducted, and total syntheses of daphenylline and lycopalhine A were accomplished. The synthesis of daphenylline features intramolecular cycloaddition of an azomethine ylide as well as a Claisen rearrangement. In these reactions, the stereochemistries were remotely controlled by the characteristic conformation of the DEF tricyclic core. The synthesis of lydopalhine A features construction of the tricyclic system via cleavage of a cyclopropane ring and a subsequent intramolecular Michael addition. We also carried out synthetic studies of yuzurimine and obtained a key intermediate for the total synthesis, which has a tetrasubstituted C-C double bond in the [5-5] bicyclic system.

Report

(4 results)
  • 2017 Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (15 results)

All 2017 2016 2015 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 5 results) Presentation (8 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results) Remarks (2 results)

  • [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] 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 2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chemical Transformation of an Intermediate in the Synthesis of Huperzine A, Leading to a Diverse Array of Molecules2016

    • Author(s)
      Satoshi Yokoshima, Masatsugu Ishikawa, Youko Beniyama, Tohru Fukuyama
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 10 Pages: 1528-1531

    • DOI

      10.1248/cpb.c16-00507

    • NAID

      130005598027

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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] Total Synthesis of Lycpalhine A2016

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

      Organic Letters

      Volume: 18 Issue: 6 Pages: 1494-1496

    • DOI

      10.1021/acs.orglett.6b00338

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Total synthesis of Daphenylline2016

    • Author(s)
      Ryosuke Yamada, Yohei Adachi, Yokoshima Satoshi, Tohru Fukuyama
    • Organizer
      21st International Conference on Organic Synthesis
    • Place of Presentation
      Bombay, India
    • Year and Date
      2016-12-11
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic Studies on Haliclonin A2016

    • Author(s)
      折原 賢祐、河岸 文希、横島 聡、福山 透
    • Organizer
      21st International Conference on Organic Synthesis
    • Place of Presentation
      Bombay, India
    • Year and Date
      2016-12-11
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 高度縮環構造をもつ天然物の合成研究2016

    • Author(s)
      横島 聡
    • Organizer
      平成28年度後期(秋季)有機合成化学講習会
    • Place of Presentation
      東京
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Heterocyclic Natural Products2016

    • Author(s)
      Satoshi Yokoshima
    • Organizer
      The 1st M&M SYNTECH Unit International Meeting 2016
    • Place of Presentation
      Nagoya, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 含窒素多環式天然物の合成研究2016

    • Author(s)
      横島 聡
    • Organizer
      第74回パネル討論会 次世代を切り拓く全合成研究の若い力
    • Place of Presentation
      徳島
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] リコパルヒンAの合成研究2015

    • Author(s)
      越智祐司 横島聡 福山透
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] ダフェニリンの全合成2015

    • Author(s)
      山田諒介、安立庸平、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] Huperzine R の合成研究2015

    • Author(s)
      野村俊宗、横島聡、福山透
    • Organizer
      第61回日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2015-07-04
    • Related Report
      2015 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
      2016 Annual Research Report 2015 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
      2014 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi