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Development and Application of Methods for Constructing New Skeletons by Use of Ring-Rearrangement Metathesis and Biomimetic Reactions

Research Project

Project/Area Number 15K05504
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionKeio University

Principal Investigator

Takao Ken-ichi  慶應義塾大学, 理工学部(矢上), 教授 (70287481)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsメタセシス / 骨格変換 / 天然物合成 / シクロブテンカルボン酸 / ブテノリド / 生合成模倣反応 / 生物活性天然物
Outline of Final Research Achievements

In the field of synthetic organic chemistry, a revolutionary new strategy is needed to achieve “the ideal synthesis”. From this perspective, we focused on sequential metathesis and developed a novel ring-rearrangement metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a γ-butenolide. In this study, further applications of the ring-rearrangement metathesis were examined and a biomimetic reaction was used to construct more complex structures of natural products. As a result, we achieved the total synthesis and structural revision of clavilactone D. In addition, we succeeded in the synthesis of a biogenetic precursor of aquatolide.

Report

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

    (13 results)

All 2018 2017 2016 2015

All Journal Article (3 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (10 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results)

  • [Journal Article] Total Synthesis of Clavilactones2018

    • Author(s)
      Ken-ichi Takao, Kento Mori, Kenya Kasuga, Ryuki Nanamiya, Ayumi Namba, Yuuki Fukushima, Ryuichi Nemoto, Takuma Mogi, Hiroyuki Yasui, Akihiro Ogura, Keisuke Yoshida, Kin-ichi Tadano
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 13 Pages: 7060-7075

    • DOI

      10.1021/acs.joc.7b03268

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Structural Revision of Clavilactone D2017

    • Author(s)
      Takao, K.; Nemoto, R.; Mori, K.; Namba, A.; Yoshida, K. Ogura, A.
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 16 Pages: 3828-3831

    • DOI

      10.1002/chem.201700483

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] 連続オレフィンメタセシス反応を用いた天然物の全合成2015

    • Author(s)
      高尾賢一、吉田圭佑、只野金一
    • Journal Title

      有機合成化学協会誌

      Volume: 73 Pages: 1192-1199

    • NAID

      130005120152

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ゼイラニジンの全合成研究2018

    • Author(s)
      長田直朗・杉本康慎・小椋章弘・高尾賢一
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] クラビラクトンDの全合成および構造訂正2017

    • Author(s)
      森 健斗、小椋章弘、高尾賢一
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Total Synthesis of Clavilactones2017

    • Author(s)
      Ken-ichi Takao
    • Organizer
      The 13th Yonsei CBMH-Keio LCC Joint Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] アクアトリドの全合成研究2017

    • Author(s)
      甲斐大敬・山田 愛・小椋章弘・高尾賢一
    • Organizer
      第73回有機合成化学協会関東支部シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] アクアトリドの全合成研究2017

    • Author(s)
      甲斐大敬・山田 愛・小椋章弘・高尾賢一
    • 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] クラビラクトンDの全合成および構造訂正2017

    • Author(s)
      森 健斗・根本龍一・難波あゆみ・吉田圭佑・小椋章弘・高尾賢一
    • Organizer
      第112回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 天然物合成を指向した合成法の開発2016

    • Author(s)
      高尾賢一
    • Organizer
      有機合成化学協会 有機合成化学後期(秋季)講習会
    • Place of Presentation
      日本薬学会長井記念ホール(東京都・渋谷区)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ゼイラニジンの全合成研究2016

    • Author(s)
      杉本康慎、安田直彦、吉田圭佑、高尾賢一
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] アクアトリドの全合成研究2016

    • Author(s)
      山田 愛、福島悠貴、吉田圭佑、高尾賢一
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 環転位メタセシス反応を用いたゼイラニジンの全合成研究2015

    • Author(s)
      杉本康慎、安田直彦、吉田圭佑、高尾賢一
    • Organizer
      第32回有機合成化学セミナー
    • Place of Presentation
      ニューウェルシティ湯河原(静岡県・熱海市)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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