A short and practical synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid.
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.
Nie
Liang-Deng
LD
Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology, P.O. Box 363, 130 Mei-Long Road, Shanghai 200237, People's Republic of China.
Shi
Xiao-Xin
XX
Ko
Kwang Hyok
KH
Lu
Wei-Dong
WD
D000998:Antiviral Agents / Q000138:chemical synthesis*; D053139:Oseltamivir / Q000138:chemical synthesis*; D012765:Shikimic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D000998:Antiviral Agents; D053139:Oseltamivir; D012765:Shikimic Acid