Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: Asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase

被引：45

作者：

Tanaka, M

Norimine, Y

Fujita, T

Suemune, H

Sakai, K

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,FUKUOKA 81282,JAPAN

[2] KYUSHU WOMENS UNIV,KITAKYUSHU,FUKUOKA 807,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 20期

关键词：

D O I：

10.1021/jo9608230

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

7-Substituted norbornadienes were stereoselectively converted into the meso-3,5-bis(acetoxymethyl)cyclopentenes by a three-step sequence of ozorrolysis, 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.

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页码：6952 / 6957

页数：6

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