Total synthesis of (-)-normalindine via addition of metalated 4-methyl-3-cyanopyridine to an enantiopure sulfinimine

J Org Chem. 2006 Nov 10;71(23):8761-6. doi: 10.1021/jo061443+.

Abstract

A concise total asymmetric synthesis of the tetrahydronaphthyridine alkaloid (-)-normalindine has been accomplished via the addition of a laterally metalated 4-methyl-3-cyanopyridine to a sulfinimine (N-sulfinyl imine) as the key step.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imines / chemistry*
  • Molecular Conformation
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / chemistry
  • Nitriles / chemistry*
  • Pyridines / chemistry*
  • Stereoisomerism
  • Sulfonium Compounds / chemistry*

Substances

  • 4-methyl-3-cyanopyridine
  • Imines
  • Naphthyridines
  • Nitriles
  • Pyridines
  • Sulfonium Compounds
  • normalindine
  • sulfinimine