文献类型：期刊文献

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

作者：Nie, Liang-Deng[1];Shi, Xiao-Xin[1]

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

年份：2009

卷号：20

期号：1

起止页码：124

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000264650100012)，CCR-EXPANDED(收录号:WOS:000264650100012)】；

基金：We thank the Chinese National Science Foundation (No. A-20172015) and Shanghai Educational Development Foundation (The Dawn Program No. 03SG27) for the financial support of this work.

语种：英文

摘要：Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.