Stereoselective synthesis of the naturally occurring styryllactones (+)-goniofufurone and (+)-cardiobutanolide

J Org Chem. 2005 Jan 21;70(2):713-6. doi: 10.1021/jo0483116.

Abstract

The naturally occurring gamma-lactones (+)-goniofufurone 1 and (+)-cardiobutanolide 2, two pharmacologically active products from Goniothalamus species (Annonaceae), have been synthesized in enantiopure form using l-erythrulose as the chiral starting material. Key steps of these syntheses were a stereoselective anti boron aldol reaction and an asymmetric allylboration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • Annonaceae / chemistry*
  • Glycerol / analogs & derivatives*
  • Glycerol / chemical synthesis*
  • Glycerol / chemistry
  • Glycerol / isolation & purification
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Lactones
  • cardiobutanolide
  • 7-goniofufurone
  • 4-Butyrolactone
  • Glycerol