Synthesis of (±)-Epibatidine and Its Analogues
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (14) , 4600-4606
- https://doi.org/10.1021/jo9600666
Abstract
A nonopiate analgesic, epibatidine (1), isolated from the skin of the Ecuadoran poison frog was synthesized in racemic form starting from tropinone. 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 Favorskii rearrangement. Five analogues of 1 were also prepared, and their analgesic activities were evaluated.Keywords
This publication has 32 references indexed in Scilit:
- Synthesis of (+) and (−) EpibatidineSynthetic Communications, 1995
- Total Synthesis and Determination of the Absolute Configuration of EpibatidineThe Journal of Organic Chemistry, 1994
- Total Synthesis of a Frog Poison, (.+-.)-Epibatidine, a Potent Non-opioid Analgesic.CHEMICAL & PHARMACEUTICAL BULLETIN, 1994
- Synthesis and Biological Evaluation of (±)-Epibatidine and the CongenersSynlett, 1994
- The analgesic effect of epibatidine and isomersBioorganic & Medicinal Chemistry Letters, 1993
- The synthesis of (+)- and (–)-epibatidineJournal of the Chemical Society, Chemical Communications, 1993
- .beta.-Proline analogs as agonists at the strychnine-sensitive glycine receptorJournal of Medicinal Chemistry, 1992
- Favorskii reaction of 2-bromobicyclo(3.3.1)nonan-3-one.CHEMICAL & PHARMACEUTICAL BULLETIN, 1986
- The Favorskii rearrangement of 2-bromobicyclo[3.2.1]octan-3-one. The question of bishomoantiaromaticityThe Journal of Organic Chemistry, 1976
- Über die Jodierung von α‐Amino‐pyridinBerichte der deutschen chemischen Gesellschaft (A and B Series), 1925