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

Author:
Ansari, Alafia A., Vankar, Y. D.
Source:
RSC advances 2014 v.4 no.24 pp. 12555-12567
ISSN:
2046-2069
Subject:
Lewis bases, alkaloids, dihydroxylation, enzyme inhibitors, glycosidases, imino sugars, pyrrolidines, synthesis
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.
Agid:
6648428