A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate

J Org Chem. 2010 May 7;75(9):3125-8. doi: 10.1021/jo100187m.

Abstract

A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Cyclization
  • Cyclohexenes / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Humans
  • Influenza A Virus, H5N1 Subtype / enzymology
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors*
  • Oseltamivir / chemical synthesis*
  • Tartrates / chemistry*

Substances

  • Antiviral Agents
  • Cyclohexenes
  • Enzyme Inhibitors
  • Tartrates
  • cyclohexene
  • Oseltamivir
  • Neuraminidase
  • diethyl tartrate