SYNTHESES OF PSEUDO-α-D-GLUCOPYRANOSE, PSEUDO-β-D-GLUCOPYRANOSE, AND VALIDAMINE FROM D-GLUCURONOLACTONE

Abstract

Using a stereoselective nitromethane addition and a reductive elimination of an ethoxyethoxyl moiety with NaBH₄ as key steps, two optically active pseudo-sugars, pseudo-α-D-glucopyranose and pseudo-β-D-glucopyranose, were synthesized from D-glucuronolactone in favorable overall yield. Furthermore, a biologically active pseudo-aminosugar, validamine, was synthesized via a substitution reaction for an acetoxyl group at the β-position of the nitro group in the nitrocyclitol derivative which was prepared from a synthetic intermediate of pseudo-D-glucopyranose.