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J Org Chem. 1996 Oct 4;61(20):6952-6957.

Chemoenzymatic Synthesis of Antiviral Carbocyclic Nucleosides: Asymmetric Hydrolysis of meso-3,5-Bis(acetoxymethyl)cyclopentenes Using Rhizopusdelemar Lipase.

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1
Kyushu Women's University, 1-1 Jiyugaoka, Yahata-nishi, Kitakyushu 807, Japan.

Abstract

7-Substituted norbornadienes were stereoselectively converted into the meso-3,5-bis(acetoxymethyl)cyclopentenes by a three-step sequence of ozonolysis, reduction, and acetylation. Rhizopus delemar lipase (RDL)-catalyzed asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes afforded the monoalcohols of high enantiomeric purities (>95% ee) in good yields (64-95%). The obtained monoalcohols 11 and 14 could be applied for the synthesis of antiviral carbocyclic nucleosides (-)-carbovir and (-)-BCA.

PMID:
11667592
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