Synthesis of (–)-Allosamizoline, the Pseudoaminosugar Moiety of Allosamidin, a Chitinase Inhibitor

Abstract

The enantioselective synthesis of (–)-allosamizoline (2a), the aminocyclitol moiety of allosamidin (1a), was achieved by starting from D-glucosamine (3). Intramolecular nitrile oxide cycloaddition was adopted as the key step to construct a functional cyclopentane ring system with proper stereochemistry.