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Synfacts 2008(3): 0224-0224  
DOI: 10.1055/s-2008-1042662
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of ()-Epibatidine and ()-Epiboxidine

Contributor(s): Philip Kocienski, Indu Dager
A. Armstrong*, Y. Bhonoah, S. E. Shanahan
Imperial College London, UK
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Publikationsverlauf

Publikationsdatum:
21. Februar 2008 (online)

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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.