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

Y. Jagadeesh (1) , A.T. Tuan , B. Luo , A. Auberger (1) , J. Desire (1) , S. Nakagawa , A. Kato , Y. Zhang , M. Sollogoub , Y. Blériot (1)

1 IC2MP [Poitiers] - Institut de chimie des milieux et matériaux de Poitiers [UMR 7285]

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

Domaines: Catalyse

Y. Jagadeesh, A.T. Tuan, B. Luo, A. Auberger, J. Desire, et al.. gamma-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP . Organic & Biomolecular Chemistry, 2015, 13 pp.3446-3456. ⟨10.1039/c5ob00050e⟩. ⟨hal-01340188⟩