文献类型：期刊文献

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

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

年份：2012

卷号：23

期号：10

起止页码：742

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000306449900004)，CCR-EXPANDED(收录号:WOS:000306449900004)】；

基金：We are grateful to the National Natural Science Foundation of China (No. 20972048) for the financial support of this work.

语种：英文

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.