Ring expansions of beta-keto lactones with zinc carbenoids: syntheses of (+)-patulolide A and (+/-)-patulolide B.

Academic Article

Abstract

  • A one-pot ring expansion/oxidation/elimination method has been developed in which beta-keto lactones are converted efficiently to alpha,beta-unsaturated-gamma-keto lactones. The reaction can be successfully applied to a variety of ring sizes. Alkene stereochemistry is dependent upon ring size and reaction conditions. The method was applied to the synthesis of (+)-patulolide A.
  • Authors

  • Ronsheim, Matthew D
  • Zercher, Charles
  • Status

    Publication Date

  • March 7, 2003
  • Published In

    Keywords

  • Alkenes
  • Catalysis
  • Cyclization
  • Indicators and Reagents
  • Ketones
  • Lactones
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Stereoisomerism
  • Zinc
  • Digital Object Identifier (doi)

    Pubmed Id

  • 12608805
  • Start Page

  • 1878
  • End Page

  • 1885
  • Volume

  • 68
  • Issue

  • 5