Two isomeric crystalline cyclitol pentaacetates (10 and 11) were obtained after the keto carbonyl of 8 was reduced by catalytic hydrogenation in acetic acid. The minor product (10) in the mixture was presumably formed from the major product (1 1) by an acid-catalyzed acetyl migration to the hydroxy group generated in the reduction step. The stereochemistry at four of the ring carbons of 10, C-1, C-4, C-5, and C-6, was deduced after analysis of the ...
