Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.

Academic Article


  • An efficient formal synthesis of (+)-brefeldin A was accomplished through a synthetic approach that relied upon three keys steps. The five-membered ring was generated in a stereocontrolled fashion through application of a tandem conjugate addition-intramolecular cyclization method developed by Toru. Ring-closing metathesis provided access to a twelve-membered beta-keto lactone, which was ring-expanded to the alpha,beta-unsaturated-gamma-keto lactone through a zinc carbenoid-mediated reaction. Conversion of this lactone to (+)-brefeldin A has been reported previously.
  • Authors

  • Lin, Weimin
  • Zercher, Charles
  • Status

    Publication Date

  • June 8, 2007
  • Published In


  • Brefeldin A
  • Cyclization
  • Oxidation-Reduction
  • Zinc
  • Digital Object Identifier (doi)

    Start Page

  • 4390
  • End Page

  • 4395
  • Volume

  • 72
  • Issue

  • 12