Stereoselective synthesis of (+)-boronolide

J Org Chem. 2002 Sep 6;67(18):6560-3. doi: 10.1021/jo025813f.

Abstract

The delta-lactone boronolide (+)-1, a pharmacologically active, naturally occurring product, has been synthesized in enantiopure form with L-erythrulose as the chiral starting material. The key steps of the synthesis were a highly stereoselective aldol-reduction one-pot sequence, an indium-mediated diastereoselective aldehyde allylation, and a ring-closing metathesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • Cyclization
  • Lactones / chemical synthesis*
  • Lamiaceae / chemistry
  • Madagascar
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry
  • Stereoisomerism
  • Tetroses / chemistry

Substances

  • Lactones
  • Tetroses
  • boronolide
  • erythrulose