Γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP. Issue 11 (10th February 2015)

• Record Type: Journal Article
• Authors: Jagadeesh, Y.; Tran, A. T.; Luo, B.; Auberger, N.; Désiré, J.; Nakagawa, S.; Kato, A.; Zhang, Y.; Sollogoub, M.; Blériot, Y.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 11(2015)
• Page Start: 3446
• Page End: 3456
• Publication Date: 2015-02-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob00050e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Exploiting a γ-aminoalcohol rearrangement, pentahydroxylated azepanes are converted to pyrrolidines that are epimeric to homoDMDP, a potent glycosidase inhibitor. 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.