Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their halocyclitol derivatives starting from cis,cis -1,3-cyclooctadiene are reported. Reduction cyclooctene endoperoxide, obtained by photooxygenation -1,3-cyclooctadiene, with zinc yielded a diol followed acetylation the hydroxy group, which gave dioldiacetate OsO 4 /NMO oxidation. cyclooctane prepared was converted to corresponding cyclic sulfate via formation sulfite in presence catalytic RuO . reaction this nucleophilic azide reduction group provided target, 3-aminocyclooctanetriol. second key compound, bromotriol, epoxidation cyclooctenediol m -chloroperbenzoic acid hydrolysis HBr(g) methanol. Treatment bromotriol NaN 3 other desired Hydrolysis epoxides HCl(g) methanol stereospecifically chlorocyclooctanetriols.