title: Chemoenzymatic Synthesis of Antiviral Carbocyclic Nucleosides: Asymmetric Hydrolysis of meso-3,5-Bis(acetoxymethyl)cyclopentenes Using Rhizopusdelemar Lipase.
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.
authors.affiliation: Kyushu Women's University, 1-1 Jiyugaoka, Yahata-nishi, Kitakyushu 807, Japan.
authors.forename: Masakazu
authors.initials: M
authors.lastname: Tanaka
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Norimine
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Fujita
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Suemune
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Sakai