Journal of Organic Chemistry p. 7185 - 7194 (1993)
Update date:2022-09-26
Topics:
Johnson, Carl R.
Golebiowski, Adam
Steensma, Darryl H.
Scialdone, Mark A.
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.
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Doi:10.1016/S0040-4039(00)60643-3
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(1993)
