A flexible route towards five-membered ring imino sugars and their novel 2-deoxy-2-fluoro analogues

Abstract

A flexible route towards five-membered ring imino sugars starting from a chiral α,β-epoxy aldehyde has been developed. The approach relies on the use of the versatile epoxyamine intermediate 4, from which regiocontrolled epoxide opening affords diastereoselective access to trisubstituted pyrrohdines. Described here is the nucleophilic attack at C-2 of the pivotal epoxypyrrolidine 10, leading to the biologically relevant imino sugars 1,4-dideoxy-1,4-imino-D-arabinitol (2) and 1,4-dideoxy-1,4-imino-L-galactitol (3) as well as their novel 2-deoxy-2-fluoro analogues, after oxidative manipulation of the vinyl moiety. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.