A new, simple and efficient method for the synthesis of 7-azabicyclo[2.2.1]heptane derivatives: Formal total synthesis of epibatidine

Letters in Organic Chemistry

Volumn 3, Issue 11, 2006, Pages 827-830

  Gómez Sánchez, Elena ^a   Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

7 azabicyclo 2.2.1 heptanes; Alkyl N (c 3,t 4 dibromocyclohex 1 y1)carbamates; Epibatidine; N (c 3,t 4 dibromocyclohex 1 y1) 2,2,2 trifluoroacetamide

Indexed keywords

EID: 33845900754     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806779117049     Document Type: Article

References (37)

1. For some selected reviews on the chemistry and biology of epibatidine and analogues, see: (a) Carroll, F. I. Bioorg. Med. Chem Lett., 2004, 14, 1889;
2. (b) Daly, J. W. J. Med. Chem., 2003, 46, 445;
3. (c) Romanelli, M. N.; Gualteri, F. Med. Res. Rev., 2003, 23, 393;
4. (d) Broka, C. A. Med. Chem. Res., 1994, 4, 449.
5. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc., 1992, 114, 3475.
6. Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem., 1997, 40, 4169.
7. (a) Chen, Z.; Trudell, M. L. Chem. Rev., 1996, 96, 1179;
8. (b) Moreno-Vargas, A. J.; Schütz, C.; Scopelliti, R.; Vogel, P. J. Org. Chem., 2003, 68, 5632.
9. (a) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron, 1997, 53, 17177;
10. (b) Trost, B. M.; Cook, G. R. Tetrahedron Lett., 1996, 37, 7485;
11. (c) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett., 1998, 39, 2059;
12. (d) Szantay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szantay, J.; Temesvari-Major, C. E.; Blasko, G. Tetrahedron, 1996, 52, 11053;
13. (e) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc. Chem. Commun., 1994, 1775;
14. (f) Barros, M. T.; Maycock, C. D.; Ventura, M. R. Tetrahedron Lett., 1999, 40, 557;
15. (g) Aggarwal, V. K.; Olofsson, B. Angew. Chem. Int. Ed., 2005, 44, 5516;
16. (h) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun., 1997, 1857;
17. (i) Nakashima, H.; Hiroya, K.; Taniguchi, T.; Ogasawara, K. Synlett, 1999, 1405;
18. (j) Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc. Perkin Trans. 1, 1999, 1253.
19. (a) Evans, D. A.; Scheidt, K. A.; Downey, C. W. Org. Lett., 2001, 3, 3009;
20. (b) Lee, C.-L. K.; Loh, T.-P. Org. Lett., 2005, 7, 2965;
21. (c) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem., 1998, 63, 8397.
22. (a) 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;
23. (b) Pfister, J. R.; Wymann, W. E.; Weissberg, R. M.; Strosberg, A. M. J. Pharm. Sci., 1985, 74, 208;
24. (c) Ramanaiah, K. C. V.; Zhu, N.; Klein-Stevens, C; Trudell, M. L. Org. Lett., 1999, 1, 1439.
25. (a) Olivo, H. F.; Hemenway, M. S. J. Org. Chem., 1999, 64, 8968;
26. (b) Avenoza, A.; Cativiela, C.; Busto, J. H.; Peregrina, J. M. Tetrahedron Lett., 1995, 36, 7123.
27. (a) Palmgren, A.; Larsson, A. L. E.; Bäckwall, J.-E. J. Org. Chem., 1999, 64, 836;
28. (b) Cabanal-Duvillard, I.; Berrein, J.-F.; Royer, J.; Husson, H.-P. Tetrahedron Lett., 1998, 39, 5181.
29. Tachihara, T.; Watanabe, H.; Kitahara, T. Heterocycles, 2002, 57, 781.
30. Gómez-Sánchez, E.; Marco-Contelles, J. Tetrahedron, 2005, 61, 1207.
31. Kapferer, P.; Vasella, A. Helv. Chim. Acta, 2004, 87, 2764.
32. (a) Che, C.; Petit, G.; Kotzyba-Hibert, F.; Bertrand, S.; Bertrand, D.; Grutter, T.; Goeldner, M. Bioorg. Med. Chem. Lett., 2003, 13, 1001;
33. (b) Wei, Z.-L.; Petukhov, P. A.; Xiao, Y.; Tückmantel, W.; George, C.; Kellar, K. J.; Kozikowski, A. P. J. Med. Chem., 2003, 46, 921;
34. (c) Carroll, F. I.; Lee, J. R.; Navarro, H. A.; Ma, W.; Brieaddy, L. E.; Abraham, P.; Damaj, M. I.; Martin, B. R. J. Med. Chem., 2002, 45, 4755.
35. 3), 1.29-1.16 (m, 1H, H6 endo)
36. 2O), 56.1 (C4), 49.6 (C2), 43.3 (C3), 28.3 (C6), 28.1 (C5).
37. Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem., 1993, 58, 5600.