Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin

Abstract

ABSTRACT A stereodivergent approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable chiral vinyl epoxy ester and the regio- and stereospecific opening of the epoxide ring with azide. The synthesis of two piperidine iminosugars, 1-deoxy-D-altronojirimycin and 1-deoxy-D-nojirimycin, was achieved by two related routes. • The enantioselective stereodivergent synthesis for producing the piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin is reported. • The wide applicability of the proposed approach provides access to different piperidine iminosugars. • The double diastereoselective asymmetric dihydroxylation is the key step to obtain 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin precursors.