General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine

J Org Chem. 2005 Mar 18;70(6):2325-8. doi: 10.1021/jo048172s.

Abstract

[reaction: see text] Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemical synthesis*
  • Enzyme Inhibitors / chemical synthesis*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Swainsonine / chemical synthesis*

Substances

  • Enzyme Inhibitors
  • 1-Deoxynojirimycin
  • Glycoside Hydrolases
  • Swainsonine