Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E1Type II and of the 15-E2t-Isoprostanes

J Org Chem. 2008 Apr 18;73(8):3063-9. doi: 10.1021/jo702455g. Epub 2008 Mar 20.

Abstract

Syntheses of the four enantiomerically pure diastereoisomers of the phytoprostanes E1 type II and 15-E2t-isoprostanes (1-4) are described. The key steps included the preparation of the Freïmanis (+/-)-hydroxycyclopentenone 5, enzymatic resolution of this racemic hydroxycyclopentenone, Wittig and Horner-Wadsworth-Emmons (HWE) coupling reactions and finally enantioselective reductions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclopentanes / chemistry
  • Hydrogen / chemistry
  • Isoprostanes / chemical synthesis*
  • Isoprostanes / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cyclopentanes
  • Isoprostanes
  • cyclopentanone
  • Hydrogen