A short and practical synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid

J Org Chem. 2009 May 15;74(10):3970-3. doi: 10.1021/jo900218k.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Oseltamivir / chemical synthesis*
  • Shikimic Acid / chemistry*
  • Stereoisomerism

Substances

  • Antiviral Agents
  • Oseltamivir
  • Shikimic Acid