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Synthetic studies on bioactive compounds using palladium catalyzed CO insertion

Research Project

Project/Area Number 15K07408
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionShinshu University

Principal Investigator

Makabe Hidefumi  信州大学, 学術研究院農学系, 教授 (90313840)

Co-Investigator(Renkei-kenkyūsha) FUJII HIROSHI  信州大学, 学術研究院農学系, 教授 (90165340)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords天然物 / 生理活性物質 / カルボニレーション / イソクマリン / ラクトン化
Outline of Final Research Achievements

In this study, syntheses of natural products using palladium catalyzed CO insertion and cyclization were performed. As to the synthesis of isocoumarin compounds, syntheses of legioliulin, 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one, and 6,8-dimethylfusariumin which is analogue fusariumin were accomplished. During this study, concise synthesis of (+)-altholactone was also accomplished. Next, synthetic study of eupaglabric acid which is eudesmane sesquiterpene compound was tried. Allenic triflate was chosen as a precursor of cyclic acylpalladation, however, the reaction gave complex mixture. Thus, the tiflate which possesses terminal double bond was used and it gave desirable compound in 50% yield. The synthesis of eupaglabric acid is currently under way.

Report

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

    (4 results)

All 2017 2016

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

  • [Journal Article] Synthesis of Isocoumarin Compounds, 8-Hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one and Fusariumin Analog Using Palladium-catalyzed Carbonylation Trapping with O-Enolate2017

    • Author(s)
      Asai, M.; Hattori, Y.; Makabe, H.
    • Journal Title

      Heterocycles

      Volume: 94 Issue: 8 Pages: 1542-1553

    • DOI

      10.3987/com-17-13746

    • NAID

      120007099633

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of legioliulin, a fluorescent isocoumarin compound, isolated from Legionella dumoffii using cyclic acylpalladation and Heck reaction2016

    • Author(s)
      Asai, M.; Hattori, Y.; Makabe, H.
    • Journal Title

      Tetrahedrn Letters

      Volume: 57 Issue: 35 Pages: 3942-3944

    • DOI

      10.1016/j.tetlet.2016.07.064

    • NAID

      120007099651

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] パラジウム触媒を用いた環化反応によるピペリジンアルカロイドとイソクマリン化合物の合成研究2017

    • Author(s)
      浅井将貴,武本夕貴子,服部恭尚,真壁秀文
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Pd触媒による一酸化炭素挿入を用いたイソクマリン化合物legioliulinの合成研究2016

    • Author(s)
      浅井将貴,服部恭尚,真壁秀文
    • Organizer
      日本農芸化学会中部支部第177回例会
    • Place of Presentation
      名古屋大学(愛知県 名古屋市)
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report

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

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