Total Synthesis of 2-(2-Ketoalkyl)-piperidine Alkaloids (+)- Pelletierine, (+)-Haloxynine and (-)-N-Methyl-pelletierine via Regioselective Wacker Oxidation

摘要

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.