An efficient synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol and 1,4-dideoxy-1,4-imino-D- and L-xylitol from chiral aziridines

Abstract

A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol (D-AB1, 1 and L-AB1, 3) and 1,4-dideoxy-1,4-imino-D- and L-xylitol (D-DIX, 2 and L-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis. (c) 2013 Elsevier Ltd. All rights reserved.