Access to resorcylic acid lactones via phosphonate based intramolecular olefination

J Org Chem. 2010 Nov 5;75(21):7404-7. doi: 10.1021/jo100998b.

Abstract

An approach to resorcylic acid lactones is described, exploiting an intramolecular olefination reaction for the generation of the 14-membered macrolactone. The synthetic route gave zearalenone precursors, and the preparations of other RAL analogues, trans- and cis-resorcylides are included, the latter being prepared by photoisomerization of the trans-isomer. β-Haloketone derivatives were also prepared in a highly stereoselective manner by conjugate addition of chloride or bromide to the E-enone using boron trichloride and boron tribromide, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Lactones / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Organophosphonates / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Lactones
  • Organophosphonates