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

作者:Nie Liang Deng; Shi Xiao Xin*; Ko Kwang Hyok; Lu Wei Dong
来源:Journal of Organic Chemistry, 2009, 74(10): 3970-3973.
DOI:10.1021/jo900218k

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.