Diastereoselective synthesis of all eight l-hexoses from L-ascorbic acid

J Org Chem. 2006 Jan 20;71(2):693-703. doi: 10.1021/jo0521192.

Abstract

[reaction: see text] A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These alpha-hydroxy esters were transformed into four gamma-alkoxy-alpha,beta-unsaturated esters C via the intermediates B and subsequent Wittig olefination reactions. Each one of compounds C was subjected to dihydroxylation to provide a set of two diols D. Anti/syn-differentiation in diol formation was manipulated by using (DHQD)2PHAL and (DHQ)2PHAL as chiral ligands. Further two-step reaction sequence affords all eight diastereopure L-hexoses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascorbic Acid*
  • Hexoses / chemical synthesis*
  • Hexoses / chemistry*
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Hexoses
  • Indicators and Reagents
  • Ascorbic Acid