Practical synthesis of D- and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus)

被引：81
|
作者：
Jin, YH
Liu, P
Wang, JN
Baker, R
Huggins, J
Chu, CK [1 ]
机构：
[1] Univ Georgia, Coll Pharm, Athens, GA 30602 USA
[2] USA, Med Res Inst Infect Dis, Frederick, MD 21702 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期
关键词：
D O I：
10.1021/jo034999v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly efficient and practical methodology for the syntheses of D- and L-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for the synthesis of carbocyclic nucleosides, have been developed via a ring-closing metathesis reaction from D-ribose in eight steps. The utility of D- and L-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for the preparation Of D-cyclopentyl-6-azauridine 12 and D-cyclopentenyl-5-halocytosine nucleosides (33-35) using Mitsunobu reaction to introduce pyrimidine bases as potential antiviral agents. Preliminary antiviral activity against orthopox viruses (smallpox, monkeypox, and cowpox virus) of the synthesized nucleosides are described.
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收藏
页码：9012 / 9018
页数：7
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