Total synthesis of (+)-Brefeldin A

J Org Chem. 2002 Jun 14;67(12):4127-37. doi: 10.1021/jo0110855.

Abstract

The total synthesis of (+)-brefeldin A has been accomplished via 15 linear steps in a 7.9% overall yield from the known Weinreb amide 6. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton and the direct introduction of the C1-C3 acrylate moiety using a new variant of a trans-vinylogous acyl anion equivalent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Anions / chemistry
  • Brefeldin A / analogs & derivatives
  • Brefeldin A / analysis
  • Brefeldin A / chemical synthesis*
  • Catalysis
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 4-oxo-brefeldin A
  • Amides
  • Anions
  • Brefeldin A