Total synthesis of amphidinolide E

J Am Chem Soc. 2006 Dec 20;128(50):15960-1. doi: 10.1021/ja066663j.

Abstract

A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3.Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Esterification
  • Molecular Structure
  • Silanes / chemical synthesis
  • Silanes / chemistry

Substances

  • Aldehydes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Silanes
  • amphidinolide E