Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors

Abstract : The synthesis of fused bicyclic oxazolidin-2-one (OZO) iminosugars was achieved through a tandem Staudinger reduction/retro-Michael/intramolecular Michael addition from the corresponding OZO azidosugars. Those precursors, based on both aldopentofuranoses and ketofuranohexoses backbones, were obtained following alkylation and oxidation of the related oxazolidine-2-thione (OZT) azidosugars. Eight OZO based iminosugars were isolated in good yields and evaluated for their potency as glycosidases inhibitors, thus extending the family of known 1-Deoxynojirimycin (DNJ) bicyclic analogues.