A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (-)-shikimic acid

被引：26

作者：

Nie, Liang-Deng ^{[1
]}

Ding, Wei ^{[1
]}

Shi, Xiao-Xin ^{[1
]}

Quan, Na ^{[1
]}

Lu, Xia ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 10期

基金：

中国国家自然科学基金;

关键词：

NEURAMINIDASE INHIBITOR OSELTAMIVIR; POTENT ANTIINFLUENZA ACTIVITY; RING-CLOSING METATHESIS; AZIDE-FREE SYNTHESIS; SHIKIMIC ACID; CHEMOENZYMATIC SYNTHESIS; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; PRACTICAL SYNTHESIS; ETHYL-ESTER;

D O I：

10.1016/j.tetasy.2012.05.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel and high-yielding asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu(R)) is described. The target compound 1 was obtained in 55% overall yield via an 11-step asymmetric synthesis starting from the naturally abundant (-)-shikimic acid. The present synthesis is characterized by some advantages such as the easy separation of intermediate 6 from triphenylphosphine oxide by using its large water-solubility, the use of inexpensive reagents throughout the synthesis, the lack of toxic heavy metals, mild reaction conditions and high yields for all steps. The stereochemical structure of the key intermediate 6 was unequivocally confirmed by X-ray crystallographic analysis. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：742 / 747

页数：6

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