Synthesis of epibatidine isomers: Reductive Heck coupling of 2- azabicyclo[2.2.1]hept-5-ene derivatives

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11879-11888

  Cox, Caroline D ^a   Malpass, John R ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EPIBATIDINE; EPIBATIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG USE; PRIORITY JOURNAL; UNITED KINGDOM;

EID: 0033215220     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00675-4     Document Type: Article

References (18)

1. T.F. Spande, H.M. Garraffo, M.W. Edwards, H.J.C. Yeh, L. Pannell and J.W. Daly, J.Amer.Chem.Soc., 1992, 114, 3475. References to the wide range of syntheses of epibatidine will be found in, e.g. Aoyogi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem., 1998, 63, 8397; Palmgren, A.; Larsson, A.L.E.; Bäckvall, J-E.; Helquist, P. J. Org. Chem., 1999, 64, 836.
2. T.F. Spande, H.M. Garraffo, M.W. Edwards, H.J.C. Yeh, L. Pannell and J.W. Daly, J.Amer.Chem.Soc., 1992, 114, 3475. References to the wide range of syntheses of epibatidine will be found in, e.g. Aoyogi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem., 1998, 63, 8397; Palmgren, A.; Larsson, A.L.E.; Bäckvall, J-E.; Helquist, P. J. Org. Chem., 1999, 64, 836.
3. T.F. Spande, H.M. Garraffo, M.W. Edwards, H.J.C. Yeh, L. Pannell and J.W. Daly, J.Amer.Chem.Soc., 1992, 114, 3475. References to the wide range of syntheses of epibatidine will be found in, e.g. Aoyogi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem., 1998, 63, 8397; Palmgren, A.; Larsson, A.L.E.; Bäckvall, J-E.; Helquist, P. J. Org. Chem., 1999, 64, 836.
4. Holladay, M.W.; Dart, M.J.; Lynch, J.K. J. Med. Chem., 1997, 40, 4169.
5. Malpass, J.R.; Hemmings, D.A.; Wallis, A.L. Tetrahedron Letters, 1996, 37, 3911.
6. Malpass, J.R.; Hemmings, D.A.; Wallis, A.L.; Patel, S. manuscript in preparation. An alternative route to 2 has also been developed and analgesic data reported: Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem., 1996, 61, 4600.
7. Malpass, J.R.; Hemmings, D.A.; Wallis, A.L.; Patel, S. manuscript in preparation. An alternative route to 2 has also been developed and analgesic data reported: Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem., 1996, 61, 4600.
8. For work on nAChRs, see: Glennon, R.A.; Herndon, J.I.; Dukat, M. Med. Chem. Res., 1994, 4, 461; Bencherif, M.; Schmitt, J.D.; Bhatti, B.S.; Crooks, P.; Caldwell, W.S.; Lovette, M.E.; Fowler, K.; Reeves, L.; Lippiello, P.M. J. Pharmacol. Exp. Ther. 1998, 284, 886.
9. For work on nAChRs, see: Glennon, R.A.; Herndon, J.I.; Dukat, M. Med. Chem. Res., 1994, 4, 461; Bencherif, M.; Schmitt, J.D.; Bhatti, B.S.; Crooks, P.; Caldwell, W.S.; Lovette, M.E.; Fowler, K.; Reeves, L.; Lippiello, P.M. J. Pharmacol. Exp. Ther. 1998, 284, 886.
10. Malpass, J.R.; Cox, C.D. Tetrahedron Letters, 1999, 40, 1419. A preliminary account of this work was also given in a lecture at the 16th National Organic Conference of the Royal Australian Chemical Institute, Leura NSW, in July 1998 (Contributed lecture 49: Conference Abstracts, p. 75).
11. Clayton, S.C.; Regan, A.C. Tetrahedron Letters, 1993, 34, 7493.
12. Malpass, J.R.; Cox, C.D. manuscript in preparation.
13. a. Kasyan, A.; Wagner, C.; Maier, M.E. Tetrahedron, 1998, 54, 8047.
14. 9a
15. Larsen, S.D.; Grieco, P.A. J.Amer. Chem. Soc., 1985, 107, 1768.
16. For typical chemical shifts and J values in the 2-azabicyclo[2.2.1]heptane and related systems see Belkacemi, D.; Malpass, J.R. Tetrahedron, 1993, 49, 9105 and references cited therein.
17. Mason, M.R.; Verkade, J.G.; Organometallics, 1992, 11, 2212.
18. Carroll, F.I.; Abraham, P.; Chemburkar, S.; He, X-W.; Mascarella, S.W.; Kwon, Y.W.; Triggle, D.J. J. Med. Chem., 1992, 35, 2184.