4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 10, Pages 3970-3973

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo900218k

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Funding

  1. Chinese National Science Foundation [A-20172015]
  2. Shanghai Educational Development Foundation [03SG27]

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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.

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