FROM CYCLOHEPTATRIENE TO ENANTIOPURE SUGARS - SYNTHESIS OF 2-DEOXYHEXOSES

meso-Diol 3, prepared from cycloheptatriene, was desymmetrized with Ps eudomonas cepacia lipase and isopropenyl acetate to provide enantiopur e 4. The latter, through a series of stereocontrolled oxidation reacti ons, 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 cor responding alditol pentaacetates. (C) 1998 Elsevier Science Ltd. All r ights reserved.