Total Synthesis of (−)-Normalindine via Addition of Metalated 4-Methyl-3-cyanopyridine to an Enantiopure Sulfinimine

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.