From cycloheptatriene to enantiopure sugars: synthesis of 2-deoxyhexoses

meso-Diol 3, prepared from cycloheptatriene, was desymmetrized with Pseudomonas cepacia lipase and isopropenyl acetate to provide enantiopure 4. The latter, through a series of stereocontrolled oxidation reactions, followed by ring cleavage by ozonolysis and oxidative cleavage of a terminal diol with periodate, provided of 2-deoxy-d-xylo-hexose (1) and 2-deoxy-d-arabino-hexose (2), which were characterized as the corresponding alditol pentaacetates.