SYNTHESIS OF (+ -)-EPIBATIDINE AND ITS ANALOGS/

Authors
BAI DG XU R CHU GH ZHU XG
Citation
Dg. Bai et al., SYNTHESIS OF (+ -)-EPIBATIDINE AND ITS ANALOGS/, Journal of organic chemistry, 61(14), 1996, pp. 4600-4606
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
14
Year of publication
1996
Pages
4600 - 4606
Database
ISI
SICI code
0022-3263(1996)61:14<4600:SO(-AI>2.0.ZU;2-H
Abstract
A nonopiate analgesic, epibatidine (1), isolated from the skin of the Ecuadoran poison frog was synthesized in racemic form starting from tr opinone. Distinctly different-from the previously published approaches , this synthesis features the novel synthesis of the 7-azabicyclo[2.2. 1]heptane ring system by contraction of the tropinone skeleton via Fav orskii rearrangement. Five analogues of 1 were also prepared, and thei r analgesic activities were evaluated.