Abstract
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.
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