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

J Org Chem. 2003 Mar 7;68(5):1878-85. doi: 10.1021/jo0264776.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Indicators and Reagents
  • Ketones / chemistry*
  • Lactones / chemical synthesis*
  • Lactones / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Alkenes
  • Indicators and Reagents
  • Ketones
  • Lactones
  • patulolide B
  • patulolide A
  • Zinc