ENZYMATIC ASYMMETRIZATION IN ORGANIC MEDIA - SYNTHESIS OF UNNATURAL GLUCOSE FROM CYCLOHEPTATRIENE

Pseudomonas cepacia lipase mediated asymmetrization of a meso-3-O-protected 6-cyclohepten-1,3,5-triol using isopropenyl acetate as solvent produced optically pure monoacetate 2. Elaboration of 2 by stereoselective oxygenation of the ring system using the Rubottom reaction, diastereoselective reduction, and osmium tetroxide catalyzed cis hydroxylation lead to cycloheptanehexaol derivative 20. This cyclic polyol was transformed into an allylic alcohol which was subjected to ozonolysis followed by NaIO4 diol cleavage to give L-glucose.