Stereospecific synthesis of a new N-tosyl bromo-aminocyclitol

Aminocyclitols are cyclic polyhydroxylated amines formally derived from cyclitols, and they constitute an important class of biologically active compounds. In the current research, the synthesis and characterization of a new N-tosyl bromo-aminocyclitol 8 starting from cyclohexadiene were carried out. In accordance with this purpose, the oxazolidinone 13 was prepared by the palladium-catalyzed reaction of bis-carbamate 12, synthesized from cyclohexenediol, derived in two steps from cyclohexadiene. Hydrolysis of 13 was achieved with methanolic potassium carbonate to afford 14 and ketalization gave 18 with good yield. Allylic bromination of 18 gave compound 19. Bromination was conducted with N-bromosuccinimide in the presence of a catalytic amount of benzoyl peroxide. Osmylation of the double bond and acid-mediated acetonide removal of 19 gave N-((1S,2R,3R,4S,6S)-4-bromo-2,3,6-trihydroxycyclohexyl)-4-methylbenzenesulfonamide 8. This molecule may also be evaluated for its biological activity.