Synthesis of (±)-epibatidine and its analogues

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4600-4606

  Bai, Donglu ^a   Xu, Rui ^a   Chu, Guohua ^a   Zhu, Xingzu ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANALGESIC AGENT; EPIBATIDINE; MECAMYLAMINE; NICOTINIC RECEPTOR;

ANALGESIA; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; INTRAPERITONEAL DRUG ADMINISTRATION; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0344298556     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600666     Document Type: Article

References (39)

1. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannel, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
2. (a) Li, T.; Qian, C.; Eckman, J.; Huang, D. F.; Shen, T. Y. Bioorg. Med. Chem. Lett. 1993, 3, 2759.
3. (b) Qian, C.; Li, T.; Shen, T. Y.; Libertine-Garaham, L.; Eckman, J.; Biftu, T.; Ip, S. Eur. J. Pharmacol. 1993, 250, R13.
4. (c) Badio, B.; Daly, J. W. Mol. Pharmcol. 1994, 45, 563.
5. (d) Fisher, M.; Huang, D. F.; Shen, T. Y.; Guyenet, P. G. J. Pharmcol. Exp. Ther. 1994, 270, 702.
6. Javick, M. E. Br. J. Addict. 1991, 86, 571.
7. (a) Damaj, M. I.; Creasy, K. R.; Grove, A. D.; Rosecrans, J. A.; Martin, B. R. Brain Res. 1994, 664, 34.
8. (b) Rupniak, N. M. J.; Patel, S.; Marwood, R.; Webb, J.; Traynor, J. R.; Elliott, J.; Freedman, S. B.; Fletcher S. R.; Hill. R. G. Br. J. Pharmacol. 1994, 113, 1487.
9. (c) Sullivan, J. P.; Decker, M. W.; Brioni, J. D.; Donnelly-Roberts, D.; Anderson, D. J.; Bannon, A. W.; Kang, C. H.; Adams, P.; Piattoni-Kaplan, M.; Buckley, M. J.; Gopalakrishnan, M.; Williams, M.; Arneric, S. P. J. Pharmcol. Exp. Ther. 1994, 271, 624.
10. (d) Bonhaus, D. W.; Bley, K. R.; Broka, C. A.; Fontana, D. J.; Leung, E.; Lewis, R.; Shieh, A.; Wong, E. H. F. J. Pharmcol. Exp. Ther. 1995, 272, 1199.
11. (a) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477.
12. (b) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493.
13. (c) Okabe, K.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1432.
14. (d) Kotian, P. L.; Carrol, F. I. Synth. Commun. 1995, 25, 63.
15. (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251.
16. (b) Fletcher, S. R.; Baker, R.; Chambers, M. S.; Hobbs, S. C.; Mitchell, P. J. J. Chem. Soc., Chem. Commun. 1993, 1216.
17. (c) Corey, E. J.; Loh, T. E.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600.
18. (d) Fletcher, S. R.; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.; Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771.
19. (e) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Major-Temesváry, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171.
20. (f) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343.
21. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417.
22. (h) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775.
23. Xu, R.; Chu, G. H.; Bai, D. L. Tetrahedron Lett. 1996, 37, 1463.
24. Xu, R.; Bai, D. L.; Chu, G. H.; Tao, J. N.; Zhu, X. Z. Bioorg. Med. Chem. Lett. 1996, 6, 279.
25. Montzka, T. A.; Matiskella, J. D.; Rartyka, R. A. Tetrahedron Lett. 1974, 15, 1325.
26. Krow, G. R. Tetrahedron 1981, 37, 2697.
27. Itooka, T.; Matoba, K.; Yamazaki, T.; Muraoka, O.; Momose, T. Chem. Pharm. Bull. 1988, 34, 2391.
28. Chenier, P. J.; Kao, J. C. J. Org. Chem. 1976, 41, 3730.
29. It would be a more direct procedure if α,α′-dihalotropinone could be rearranged to 3 in a single step. However, all attempts by means of Favorskii rearrangement on α,α′-dibromotropinone under various basic conditions to achieve the α,β-unsaturated ester 3 were unsuccessful.
30. (a) Arcadi, A.; Marinelli, F.; Bernocchi, E.; Cacchi, S.; Ortar, G. J. J. Organomet. Chem. 1989, 368, 249.
31. (b) Larock, R. C.; Johnson, P. L. J. Chem. Soc., Chem. Commun. 1989, 1368.
32. Magidson, O.; Menschikoff, G. Chem. Ber. 1925, 58, 113.
33. Gonzalez, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405.
34. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
35. Jones, J. B.; Pinder, A. R. J. Chem. Soc. 1959, 615.
36. (a) Johnson, G.; Drummond, J. T.; Boxer, P. A.; Bruns, R. F. J. Med. Chem. 1992, 35, 233.
37. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pham. Bull. 1985, 33, 2762 and references cited therein.
38. Kawaguchi, M.; Hayashi, O.; Kanamoto, M.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem. 1987, 51, 435.
39. Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.