Lipase-Mediated Preparation of A Functionalized Bicyclo[3,2,1]octenone and A Practical Utilization

Hiroshi Nagata; Norio Miyazawa; Kunio Ogasawara

doi:10.1055/s-2000-8717

Synthesis 2000; 2000(14): 2013-2018
DOI: 10.1055/s-2000-8717

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Lipase-Mediated Preparation of A Functionalized Bicyclo[3,2,1]octenone and A Practical Utilization

Hiroshi Nagata^* , Norio Miyazawa, Kunio Ogasawara

^*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81(22)2 17 68 45; E-mail: konol@mail.cc.tohoku.ac.jp

Abstract

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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

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