Efficient short step synthesis of Corey's tamiflu intermediate

Org Lett. 2008 Mar 6;10(5):815-6. doi: 10.1021/ol7029646. Epub 2008 Jan 26.

Abstract

Corey's tamiflu intermediate was synthesized from a bicyclolactam adduct obtained by base-catalyzed Diels-Alder reaction of N-nosyl-3-hydroxy-2-pyridone with ethyl acrylate. A compound that has the same array of functional groups with the Corey's intermediate was obtained in four steps from the DA adduct in 47% overall yield. The intermediate itself was also prepared efficiently by simply changing the protective group.

MeSH terms

  • Catalysis
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors
  • Oseltamivir / analogs & derivatives*
  • Oseltamivir / chemical synthesis*
  • Oseltamivir / chemistry

Substances

  • Enzyme Inhibitors
  • Oseltamivir
  • Neuraminidase