Straightforward synthesis of panaxytriol: an active component of Red Ginseng

J Org Chem. 2003 May 30;68(11):4519-22. doi: 10.1021/jo0341665.

Abstract

A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkynes
  • Catalysis
  • Enediynes
  • Fatty Alcohols / analysis
  • Fatty Alcohols / chemical synthesis*
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Panax / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Enediynes
  • Fatty Alcohols
  • Indicators and Reagents
  • panaxytriol