Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

Abstract

A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.