New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

2008-09-04T00:00:00Z (GMT) by Ying Zhou Paul V. Murphy
The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from d-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.