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Development of efficient synthetic method for novel tricyclic polyketide possessing antitumor activity

Research Project

Project/Area Number 25860012
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Kobayashi Toyoharu  東京薬科大学, 生命科学部, 助教 (40570883)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords合成化学 / 有機化学 / 海洋天然物 / 三環性ポリケチド / インドキサマイシンF
Outline of Final Research Achievements

Synthetic study of new tircyclic polyketide, indoxamycin F, possessed antitumor activity was occurred. The bicyclic skeleton of indoxamycin F was constructed through the six steps operations including Claisen rearrangement and the ring closing methathesis with Grubbs catalyst second generation from (-)-carvone. Futhermore, from resulting compound, the synthesis of bicyclic compound corresponding AB ring system of indoxamycin F was achieved through the six steps operations including diastereoselective introduction of methyl group to two a-positions of carbonyl groups. Then, from this bicyclic compound, the stereocontrolled construction of tricyclic skeleton of indoxamycin F was realized by the hemiacetal formation via reduction of ester and ketone group. The further investigation toward the total synthesis of indoxamycin F has been in progress.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (3 results)

All 2015 2013 Other

All Presentation (3 results) (of which Int'l Joint Research: 1 results)

  • [Presentation] Synthetic study of new polyketide indoxamycin F:stereocontrolled construction of tricyclic framework using Claisen rearrangement2015

    • Author(s)
      Toyoharu Kobayashi, Sayo Yamashita, Hideki Abe, Hisanaka Ito
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Indoxamycin Fの不斉合成研究2013

    • Author(s)
      山下聡淑,小林豊晴,阿部秀樹,伊藤久央
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 新規三環性ポリケチドindoxamycinFの不斉合成研究

    • Author(s)
      山下聡淑,小林豊晴,阿部秀樹,伊藤久央
    • Organizer
      第66回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京工業大学
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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