A Short and Practical Synthesis of Oseltamivir Phosphate (Tamiflu) from (-)-Shikimic Acid

被引：88
|
作者：
Nie, Liang-Deng [1 ]
Shi, Xiao-Xin [1 ]
Ko, Kwang Hyok [1 ]
Lu, Wei-Dong [1 ]
机构：
[1] E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 10期
基金：
美国国家科学基金会;
关键词：
NEURAMINIDASE INHIBITOR OSELTAMIVIR; POTENT ANTIINFLUENZA ACTIVITY; SHIKIMIC ACID; ASYMMETRIC-SYNTHESIS; CONCISE SYNTHESIS; INFLUENZA; (-)-OSELTAMIVIR; BIOSYNTHESIS; THERAPY; DESIGN;
D O I：
10.1021/jo900218k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oseltamivir phosphate (1) was synthesized from (-)-shikimic acid through a short and practical synthetic route via eight steps in 47% overall yield. In addition, the highly regioselective and stereoselective nucleophilic replacement of OMs by the N-3 group in the third and seventh steps has been studied in detail, and the reaction conditions were optimized.
引用
收藏
页码：3970 / 3973
页数：4
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