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P-60 Synthetic Study of 13-Oxyingenol(Poster Presentation)

DOI
  • Ohyoshi Takayuki
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Miyazawa Yamato
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Haruna Toshihiro
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Asuma Yuki
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Aoki Kenta
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Ohmura Satomi
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Hayakawa Ichiro
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Kigoshi Hideo
    Graduate School of Pure and Applied Sciences, University of Tsukuba

Bibliographic Information

Other Title
  • P-60 抗HIV活性物質13-オキシインゲノールの合成研究(ポスター発表の部)

Abstract

13-Oxyingenol (1) and ingenol (2) are diterpenoids isolated from the plants of Euphorbia sp. They and their analogs have interesting bioactivities. Particularly, 13-oxyingenol derivatives such as RD4-2138 have a strong anti-HIV activity. The structural features of ingenol and 13-oxyingenol are a high degree of oxygenation and a highly strained inside-outside bicylcic ring system. The molecular complexity of ingenol derivatives, in conjunction with their potent biological activities, has made them attractive synthetic targets. We planed the synthesis of 13-oxyingenol (1) by using ring-closing olein metathesis strategy. The starting point for this work was the construction of the β-ketoester 3 from 2-(4-hydroxyphenyl)ethanol. We stereoselectively introduced the methyl group to C-11 by using diastereoselective hydrogenation, to give β-ketoester 3 with desired stereochemistry. Then, we achieved the construction of the full carbon framework of 13-oxyingenol by using intramolecular spirocyclization and ring closing olefin metathesis as key steps. Further approach to 13-oxyingenol is currently underway in our group and will be reported in the symposium.

Journal

Details

  • CRID
    1390001206078484736
  • NII Article ID
    110007066659
  • DOI
    10.24496/tennenyuki.50.0_719
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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