A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: application to the total synthesis of amphiasterin B4

J Org Chem. 2009 Mar 6;74(5):2257-60. doi: 10.1021/jo8020659.

Abstract

The first total synthesis of amphiasterin B4, a secondary metabolite previously isolated from Plakortis quasiamphiaster has been achieved. The core structure has been reached according to a highly stereoselective one-pot epoxidation/cyclization of an unsaturated diol. This substrate can be prepared from beta,gamma-unsaturated diesters readily available from the organocatalyzed protonation of a transient dienol generated by UV irradiation of corresponding alpha,beta-unsaturated isomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Plakortis / chemistry*
  • Species Specificity
  • Stereoisomerism

Substances

  • Furans
  • amphiasterin B4