SYNTHESES OF VALIDAMINE, EPI-VALIDAMINE, AND VALIENAMINE, THREE OPTICALLY ACTIVE PSEUDO-AMINO-SUGARS, FROM D-GLUCOSE

Abstract

Using as a key reaction a Michael-type addition reaction to nitroolefins or a substitution reaction for an acetoxyl residue at the β-position of the nitro group in pseudo-nitro-sugar, three optically active pseudo-amino-sugars: validamine, epi-validamine, and valienamine, were synthesized from D-glucose.