Stereoselective anti aldol reactions of erythrulose derivatives. Functionalized chiral d3 and d4 synthons

J Org Chem. 2004 Mar 19;69(6):1987-92. doi: 10.1021/jo0356356.

Abstract

An improved procedure for the synthesis of anti aldols from protected erythrulose derivatives is reported. The preparation of functionalized d3 and d4 synthons with various stereochemical arrays by means of this methodology is described and subsequently applied to a stereoselective formal synthesis of the natural metabolite goniothalesdiol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / antagonists & inhibitors
  • Aldehydes / chemistry*
  • Ketones / chemistry
  • Lactones / chemical synthesis
  • Molecular Structure
  • Stereoisomerism
  • Tetroses / chemical synthesis
  • Tetroses / chemistry*

Substances

  • Aldehydes
  • Ketones
  • Lactones
  • Tetroses
  • erythrulose
  • 3-hydroxybutanal