Total Synthesis and Determination of the Absolute Configuration of Epibatidine

The synthesis of (+)- and (-)-epibatidine (exo-2-(2-chloropyridin-5-yl)-7-azabicyclo[2.2.1]heptane) via reaction of 5-lithio-2-chloropyridine with (+)- and (-)-N-BOC-7-azabicyclo [2.2.1]heptan-2-one is described. The absolute configuration of the natural product is shown to be 1R,2R,4S