title: Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.
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 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.affiliation: Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.
authors.forename: Weimin
authors.initials: W
authors.lastname: Lin
authors.forename: Charles K
authors.initials: CK
authors.lastname: Zercher
mesh_terms: D020126:Brefeldin A / Q000138:chemical synthesis*; D003500:Cyclization; D010084:Oxidation-Reduction; D015032:Zinc / Q000737:chemistry*
chemical_list: D020126:Brefeldin A; D015032:Zinc