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

Organic & biomolecular chemistry 2015 Mar 21

filter terms:

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.

Citation

Y Jagadeesh, A T Tran, B Luo, N Auberger, J Désiré, S Nakagawa, A Kato, Y Zhang, M Sollogoub, Y Blériot. γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP. Organic & biomolecular chemistry. 2015 Mar 21;13(11):3446-56