Cleavage of validoxylamine A derivatives with N-bromosuccinimide: preparation of blocked synthons useful for the construction of carba-oligosaccharides composed of imino linkages

Abstract

Reaction of validoxylamine A and several of its derivatives with N-bromosuccinimide proceeded through cleavage of the imino bonds to give rise to the synthetically useful blocked derivatives of valienamine and validamine, and the cyclohexanone and cyclohexenone derivatives. Some carbatrehalose derivatives were readily prepared by coupling of a pair of these compounds by reductive alkylation with sodium cyanoborohydride.