Formal Synthesis of (+)-Brefeldin A: Application of a Zinc-mediated Ring Expansion Reaction

Authors

Weimin Lin, University of New HampshireFollow
Charles K. Zercher, University of New HampshireFollow

Abstract

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 β-keto lactone, which was ring-expanded to the α,β-unsaturated-γ-keto lactone through a zinc carbenoid-mediated reaction. Conversion of this lactone to (+)-brefeldin A has been reported previously.

Department

Chemistry

Publication Date

6-1-2007

Journal Title

Journal of Organic Chemistry

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/jo0701379

Document Type

Article

Recommended Citation

Formal Synthesis of (+)-Brefeldin A: Application of a Zinc-mediated Ring Expansion Reaction, Lin, W.; Zercher, C. K. J. Org. Chem. 2007, 72, 4390-4395. PMCID: PMC2572133

Rights

Copyright © 2007, American Chemical Society