Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars

An efficient.one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycoidesides vetsatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars Under reagent-free conditions the N-ally]-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furniShed cyclopropane-fused iminosugar. The N-propargyl-C-nitromethyl glycosides underwent an unprecedented ketenimine-acrylamidine-Michael addition cascade reaction to give bicyclic amidines.