文献类型：期刊文献

英文题名：Novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid via cyclic sulfite intermediates

作者：Nie, Liang-Deng[1];Shi, Xiao-Xin[1];Quan, Na[1];Wang, Fei-Feng[1];Lu, Xia[1]

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

年份：2011

卷号：22

期号：16-17

起止页码：1692

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000298220200017)，CCR-EXPANDED(收录号:WOS:000298220200017)】；

基金：We thank the National Natural Science Foundation of China (No. 20972048) and Shanghai Educational Development Foundation (The Dawn Program: No. 03SG27) for the financial support of this work.

语种：英文

摘要：A novel asymmetric synthesis of oseltamivir phosphate 1 from the naturally abundant (-)-shikimic acid via 3,4-cyclic sulfite intermediate 3 (Scheme 1) is described. Target compound 1 was obtained in 39% overall yield from this nine-step synthesis, and the characteristic step of the synthesis is the regio- and stereospecific nucleophilic substitution with sodium azide at the allylic (C-3) position of 3,4-cyclic sulfite 3. Since the yield of the direct-aziridine-formation from the unprotected dihydroxyl azide 4 was not satisfactory, two improved preparations of the established compound 7 via protected 3,4-cyclic sulfites to and 13 (Scheme 2) have been developed. In these two improved preparations, compound 7 was obtained from 3,4-cyclic sulfite 3 in 7-steps in 64% or 62% overall yield, respectively. (C) 2011 Elsevier Ltd. All rights reserved.