A five-step synthesis of (±)-tylophorine via a nitrile-stabilized ammonium ylide

J Org Chem. 2012 Aug 3;77(15):6620-3. doi: 10.1021/jo3011045. Epub 2012 Jul 19.

Abstract

The Stevens rearrangement of a nitrile-stabilized ammonium ylide is the key step of a very short and practical synthesis of the phenanthroindolizine alkaloid (±)-tylophorine. The method requires only five linear steps and is devoid of any protecting group manipulations.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Indolizines / chemical synthesis*
  • Indolizines / chemistry
  • Molecular Structure
  • Nitriles / chemistry*
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Alkaloids
  • Indolizines
  • Nitriles
  • Phenanthrenes
  • Quaternary Ammonium Compounds
  • tylophorine