Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

被引：17
|
作者：
Boyle, Grant A. [1 ]
Edlin, Christopher D. [1 ]
Li, Yongfeng [2 ]
Liotta, Dennis C. [2 ]
Morgans, Garreth L. [1 ]
Musonda, Chitalu C. [1 ]
机构：
[1] IThemba Pharmaceut PTY Ltd, ZA-1645 Gauteng, South Africa
[2] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 09期
关键词：
ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; HYDROLYSIS; POTENT; HIV; RESOLUTION; INHIBITOR; 1592U89; ANALOG;
D O I：
10.1039/c2ob06775g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantiopure beta-lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a pi-allylpalladium mediated reaction with 2,6-dichloropurine tetrabutylammonium salt to afford an advanced cis-1,4-substituted cyclopentenoid with both high regio- and stereoselectivity. This advanced intermediate was successfully manipulated to the total synthesis of (-)-Abacavir.
引用
收藏
页码：1870 / 1876
页数：7
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