Total synthesis of 2-(2-Ketoalkyl)-piperidine alkaloids (+)- pelletierine, (+)-haloxynine and (-)-N-methyl-pelletierine via regioselective Wacker oxidation

Abstract

A practical synthesis of naturally occurring piperidine alkaloids (+)-pelletierine, (+)-haloxynine and (-)-N-methyl-pelletierine is described from (-)-pipecolinic acid using Wittig reaction and Wacker oxidation as the key steps. The protocol exploits the regioselective oxidation of the internal olefins.