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Issue 11, 2015
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γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

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Abstract

A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

Graphical abstract: γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

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Article information


Submitted
09 Jan 2015
Accepted
28 Jan 2015
First published
29 Jan 2015

Org. Biomol. Chem., 2015,13, 3446-3456
Article type
Paper

γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

Y. Jagadeesh, A. T. Tran, B. Luo, N. Auberger, J. Désiré, S. Nakagawa, A. Kato, Y. Zhang, M. Sollogoub and Y. Blériot, Org. Biomol. Chem., 2015, 13, 3446
DOI: 10.1039/C5OB00050E

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