• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of the synthetic method for natural compound based on the intramolecular aldol reaction

Research Project

Project/Area Number 24590023
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

HISANAKA Ito  東京薬科大学, 生命科学部, 教授 (70287457)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords全合成 / 生理活性物質 / 天然有機化合物 / 不斉合成 / 分子内アルドール反応
Outline of Final Research Achievements

Bioactive polyfunctionalized cyclic terpenoid has much attention on developing of medicine. Synthetic study of terpenoid which having complex carbon skeleton is very important for clarify the structure-activity relationship. Synthetic study of two terpenoids, albaflavenone and aberrarone, which having complex and interesting carbon skeleton, was examined. Total synthesis of albaflavenone, antibiotic sesquiterpene, has been accomplished via the concise construction of skeleton utilizing sequential intramolecular aldol condensation. This synthetic work was completed in nine steps without the use of protecting groups and with high stereocontrol. Highly stereocontrolled synthesis of the tetracyclic core of diterpenoid aberrarone, which possesses antimalarial activity, has also been accomplished. A key feature of the synthesis is the complete stereocontrolled construction of C- and D-ring using stereoselective 1,4-addition followed by intramolecular aldol reaction.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (6 results)

All 2014 2013 2012 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (5 results)

  • [Journal Article] Concise Total Synthesis of Albaflavenone utilizing Sequential Intramolecular Aldol Condensation: Determination of Absolute Configuration2014

    • Author(s)
      Toyoharu Kobayashi, Yutaro Kon, Hideki Abe, Hisanaka Ito
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 24 Pages: 6397-6399

    • DOI

      10.1021/ol503202d

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Albaflavenoneの全合成2013

    • Author(s)
      今祐太郎,阿部秀樹,小林豊晴,伊藤久央
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] AberraroneのABC環部構築法の開発研究2013

    • Author(s)
      槌谷悠紀,小林豊晴,阿部秀樹,伊藤久央
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] (±)-Albaflavenoneの全合成2012

    • Author(s)
      今祐太郎,阿部秀樹,小林豊晴,伊藤久央
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京(船堀)
    • Related Report
      2012 Research-status Report
  • [Presentation] AberraroneのABC環部の合成研究

    • Author(s)
      徳本果純,槌谷悠紀,小林豊晴,阿部秀樹,伊藤久央
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Total Synthesis of Rcemic Albaflavenone

    • Author(s)
      Yutaro Kon, Toyoharu Kobayashi, Hideki Abe, and Hisanaka Ito
    • Organizer
      The 11th International Symposium on Advanced Technology
    • Place of Presentation
      東京(八王子)
    • Related Report
      2012 Research-status Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi