A flexible synthesis of the phytoprostanes B1 type I and II

J Org Chem. 2005 Feb 4;70(3):989-97. doi: 10.1021/jo048179+.

Abstract

Syntheses of the enantiomerically pure phytoprostanes B(1) type I and II are described starting from furfural and n-propylfuran. Key steps include the preparation of the Freimanis (+/-)-hydroxycyclopentenone and Wittig coupling using chiral phosphonium salts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Fatty Acids, Unsaturated
  • Furaldehyde / chemistry
  • Furaldehyde / metabolism
  • Furans / chemical synthesis*
  • Furans / chemistry*
  • Furans / metabolism
  • Stereoisomerism

Substances

  • Alkenes
  • Fatty Acids, Unsaturated
  • Furans
  • phytoprostane B1 type I
  • phytoprostane B1 type II
  • Furaldehyde