A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid

作者：Nie Liang Deng; Shi Xiao Xin^*

来源：Tetrahedron: Asymmetry , 2009, 20(1): 124-129.

DOI：10.1016/j.tetasy.2008.11.027

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.

• 出版日期2009-1-30
• 单位华东理工大学