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; Y. Blériot

doi:10.1039/C5OB00050E

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

Y. Jagadeesh,^a A. T. Tran,^b B. Luo,^b N. Auberger,^a J. Désiré,^a S. Nakagawa,^c A. Kato,^c Y. Zhang,^b M. Sollogoub^b and Y. Blériot*^a

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^a Glycochemistry Group of “Organic Synthesis” Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France
E-mail: yves.bleriot@univ-poitiers.fr
Tel: +33 5 49453966

^b Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR-CNRS 8232, IPCM, LabEx MiChem, F-75005 Paris, France

^c Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

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.

Organic & Biomolecular Chemistry

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

Abstract

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

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