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Synthetic study of the antitumor tricyclic diterpenoides

Research Project

Project/Area Number 26460016
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

ABE Hideki  東京薬科大学, 生命科学部, 准教授 (00328551)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordscurcusone / Weinreb アミド化 / 7員環構築 / Dowd-Beckwith環拡大反応 / 向山 aldol 反応 / ケタール化 / afritoxinone A / catunaregin / ワインレブアミド化 / ドード-ベックウィズ環拡大反応 / 向山アルドール反応 / 三環性ジテルペノイド / 抗腫瘍活性 / トウダイグサ科 / Jatropha curcus
Outline of Final Research Achievements

Synthetic study of tricyclic diterpenoid curcusones possess antitumor activity were demonstrated. For the reason that the polycyclic acetal compound was obtained instead of the desired product at the synthetic study of key intermediate lactone, the ring expansion reaction was performed as a new synthetic pathway to construct a seven-membered ring. Furthermore, the construction of the tricyclic skeleton of target natural compound curcusones was accomplished with several procedures including Mukaiyama aldol reaction.
On the other hand, construction of polyoxygenated framework of afritoxinone A and efficient asymmetric total synthesis of catunaregin were achieved based on the side reaction at the synthetic study of lactone moiety.

Report

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

    (6 results)

All 2017 2016 2015 2014

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 2 results,  Open Access: 1 results) Presentation (4 results)

  • [Journal Article] Concise asymmetric total synthesis of catunaregin2016

    • Author(s)
      Hideki Abe, Takuma Hikichi, Kosuke Emori, Toyoharu Kobayashi, and Hisanaka Ito
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 3 Issue: 9 Pages: 1084-1086

    • DOI

      10.1039/c6qo00213g

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic study of afritoxinone A: Stereoselective construction of furopyranone moiety2015

    • Author(s)
      Hideki Abe, Toshihiro Yoshie, Takumi Wagatsuma, Toyoharu Kobayashi, and Hisanaka Ito
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 706-714

    • DOI

      10.3987/com-14-s(k)40

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] カルカソン類の合成研究2017

    • Author(s)
      阿部秀樹、井出義磨、小林豊晴、伊藤久央
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] 三環性ノルネオリグナン catunaregin の不斉全合成2016

    • Author(s)
      曵地琢摩、阿部秀樹、小林豊晴、伊藤久央
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] マングローブ由来ノルネオリグナン catunaregin の全合成2015

    • Author(s)
      曵地琢摩、阿部秀樹、江森皓亮、小林豊晴、伊藤久央
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] アフリトキシノン A の合成研究2014

    • Author(s)
      阿部秀樹,吉江敏洋,我妻巧,小林豊晴,伊藤久央
    • Organizer
      第 44 回複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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