High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations

Angew Chem Int Ed Engl. 2009;48(7):1304-7. doi: 10.1002/anie.200804883.

Abstract

Taking shortcuts: A remarkably short and high-yielding asymmetric total synthesis of (-)-oseltamivir takes advantage of organocatalysis and single-pot domino operations. The target, known as the drug Tamiflu, is prepared efficiently in a short time, and also its derivatives can be synthesized effectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / therapeutic use
  • Catalysis
  • Ethers / chemistry
  • Humans
  • Influenza, Human / drug therapy*
  • Oseltamivir / analogs & derivatives
  • Oseltamivir / chemical synthesis*
  • Oseltamivir / therapeutic use
  • Proline / analogs & derivatives
  • Proline / chemistry
  • Stereoisomerism

Substances

  • Antiviral Agents
  • Ethers
  • diphenylprolinol silyl ether
  • Oseltamivir
  • Proline