Synthesis of pyrrolidine iminosugars, (?)-lentiginosine, (?)-swainsonine and their 8a-epimers from d-glycals?

RSC Advances Pub Date: 2014-01-20 DOI: 10.1039/C3RA47555G

Abstract

Synthesis of pyrrolidine iminosugars has been described from D-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (?)-lentiginosine and (?)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.

Graphical abstract: Synthesis of pyrrolidine iminosugars, (?)-lentiginosine, (?)-swainsonine and their 8a-epimers from d-glycals
Recommended Literature