41 Total Synthesis of 13-Oxyingenols(Oral Presentation)

DOI
  • Ohyoshi Takayuki
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Funakubo Shota
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Miyazawa Yamato
    Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Niida Keisuke
    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
  • 41 13-オキシインゲノール類の全合成(口頭発表の部)

Abstract

13-Oxyingenol derivative 1 and ingenol (3) are diterpenoids isolated from the plants of Euphorbia sp. The main structural features of ingenols are a bicyclo[4.4.1]undecane skeleton with inside-outside intrabridgehead stereochemistry and a high degree of oxygenation. They and their analogues showed interesting bioactivities. The molecular complexity of ingenol derivatives, in conjunction with their potent bioactivities, has made them attractive synthetic targets. We have achieved the first total synthesis of (-)-13-oxyingenol (2) and its natural derivative 1. The efficient functionalization of the A- and B-ring parts was established by using C-2 and C-7 hydroxy groups as clues. This approach is highlighted by RCM for the construction of an inside-outside framework, regio- and stereoselective dihydroxylation for the functionalization of the A-ring, and [2,3]-sigmalropic rearrangement for the functionalization of the B-ring.

Journal

Details 詳細情報について

  • CRID
    1390282681056354176
  • NII Article ID
    110010013834
  • DOI
    10.24496/tennenyuki.54.0_241
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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