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

摘要

A highly efficient method for the synthesis of l,4-dideoxy-l,4-imino-D-and L-arabinitol (d-AB1, 1 and l-ABI, 3) and l,4-dideoxy-l,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.