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Issue 24, 2014

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

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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

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Article information


Submitted
12 Dec 2013
Accepted
17 Jan 2014
First published
20 Jan 2014

RSC Adv., 2014,4, 12555-12567
Article type
Paper

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

A. A. Ansari and Y. D. Vankar, RSC Adv., 2014, 4, 12555 DOI: 10.1039/C3RA47555G

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