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Synthetic studies on marine-derived polyketides that exhibit proliferation-promoting activity on osteoblastic cells and bone marrow stromal cells

Research Project

Project/Area Number 15K14718
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

Kuwahara Shigefumi  東北大学, 農学研究科, 教授 (30170145)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsamphirionin / total synthesis / osteoblast / polyketide / 生体分子 / 生理活性 / 有機化学
Outline of Final Research Achievements

Total synthetic studies on amphirionin-4 (1) and amphirionin-5 (2), which exhibit potent proliferation-promoting activity on osteoblastic cells and related cells, were conducted. As for 1, its expeditions enantioselective total synthesis was achieved by an 8-pot sequence that features a concise construction of an all-cis trisubstituted THF ring using a diastereoselective iodoetherification and a lactone-forming intramolecular alkylation to connect the left-hand and central moieties of the target molecule. Our efforts toward the preparation of the C1-C8 fragment of 2 are now underway.

Report

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

    (5 results)

All 2016

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (4 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Total synthesis of amphirionin-52016

    • Author(s)
      Yusuke Ogura, Hikaru Sato, Shigefumi Kuwahara
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 10 Pages: 2399-2402

    • DOI

      10.1021/acs.orglett.6b00883

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Amphirionin-4の全合成2016

    • Author(s)
      小倉由資,佐藤光,桑原重文
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学川内萩ホール(宮城県仙台市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthetic study of amphirionin-4: proliferative natural product against osteoplastry-related cells2016

    • Author(s)
      Hikaru Sato, Yusuke Ogura, Shigefumi Kuwahara
    • Organizer
      Campus Asia Program: Tohoku University’s Chemistry Summer School 2016
    • Place of Presentation
      東北大学理学研究科(宮城県仙台市)
    • Year and Date
      2016-08-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 骨形成関連細胞増殖物質amphirionin-4の全合成研究2016

    • Author(s)
      佐藤光,小倉由資 ,桑原重文
    • Organizer
      第109回有機合成シンポジウム
    • Place of Presentation
      東京工業大学大岡山キャンパス(東京都目黒区)
    • Year and Date
      2016-06-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] Amphirionin-4の不斉全合成2016

    • Author(s)
      小倉由資,佐藤光,桑原重文
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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