Total synthesis of the eight diastereomers of the syn-anti-syn phytoprostanes F1 types I and II

J Org Chem. 2004 Apr 2;69(7):2498-503. doi: 10.1021/jo035638i.

Abstract

Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F(1) types I and II are described starting from D- and L-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of alpha,beta-unsaturated ketones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclopentanes / chemical synthesis*
  • F2-Isoprostanes / chemical synthesis*
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Indicators and Reagents
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Cyclopentanes
  • F2-Isoprostanes
  • Fatty Acids, Unsaturated
  • Indicators and Reagents
  • phytoprostane F1