Efficient formal synthesis of oseltamivir phosphate (Tamiflu) with inexpensive D-ribose as the starting material

Org Lett. 2010 Jan 1;12(1):60-3. doi: 10.1021/ol9024716.

Abstract

An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / economics
  • Catalysis
  • Molecular Structure
  • Oseltamivir / chemical synthesis*
  • Oseltamivir / chemistry
  • Oseltamivir / economics
  • Ribose / chemistry*
  • Stereoisomerism

Substances

  • Antiviral Agents
  • Oseltamivir
  • Ribose