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

Abstract

(Chemical Equation Presented) Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbarnate 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. © 2005 American Chemical Society.