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Lipase-Mediated Preparation of A Functionalized Bicyclo[3,2,1]octenone and A Practical Utilization
31 December 2000 (online)
Both enantiomers of a functionalized bicyclo[3.2.1]octane molecule potentially useful as a versatile chiral building block have been prepared in enantiomerically pure forms from norbornadiene by employing lipase-mediated kinetic resolution. By transforming both enantiomers enantioconvergently into the same chiral lactone serving as the key intermediate for the synthesis of the naturally occurring carbocyclic nucleoside (-)-aristeromycin, the absolute configuration of the resolved products has been established and at the same time their synthetic potential has been demonstrated.
chiral building block - enzymes - lipase-mediated kinetic resolution - carbocyclic nucleoside - enantioconvergent synthesis - aristeromycin