Enantio- and Diastereoselective Transformations of Cycloheptatriene to Sugars and Related Products

Article abstract of DOI:10.1021/jo00077a049

Both meso diastereomers of 6-<(tert-butyldimethylsilyl)oxy>-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate.A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monoacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.