Syntheses of ()-Epibatidine and ()-Epiboxidine

Significance

Epibatidine, an alkaloid isolated from the skin of the Equadorian poison frog Epipedobates tricolor, is a potent analgesic and acts as a nicotine agonist. Reported here is the synthesis of ()-epibatidine and its analogue ()-epiboxidine starting from the same intermediate 7-azabicyclo[2.2.1]heptane D which was synthesized by an aza-Prins-pinacol rearrangement as the key step.