The synthesis of new heterocyclic bridged ring systems. Analogs of tetrahydro-β-carbolines

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1441-1444

  Gremmen, Christiaan ^a   Burm, Brigitte E A ^a   Wanner, Martin J ^a   Koomen, Gerrit Jan ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; BRIDGED COMPOUND; HETEROCYCLIC COMPOUND; TRYPTOLINE;

ARTICLE; POLYMERIZATION; SYNTHESIS;

EID: 0032510427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10823-1     Document Type: Article

References (19)

1. 1. Agarwal, A.; Pearson, P. P.; Taylor, E. W.; Li, H. B.; Dahlgren, T.; Herslöf, M.; Yang, Y.; Lambert, G.; Nelson, D. L.; Regan, J. W.; Martin, A. R. J. Med. Chem. 1993, 36, 4006-4014.
2. 2. (a) Bailey, P. D.; Collier, I. D.; Hollinshead, S. P.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. J. Chem. Soc. Perkin Trans. I 1997, 1209-1214.
3. (b) Bi, Y; Zhang, L.-H.; Hamaker, L. K.; Cook, J. M. J. Am. Chem. Soc. 1994, 116, 9027-9041.
4. 3. Üstünes, L.; Özer, A.; Laekeman, G. M.; Corthout, J.; Pieters, L. A. C.; Baeten, W.; Herman, A. G.; Claeys, M.; Vlietinck, A. J. J. Nat. Prod. 1991, 54, 959-966.
5. 4. Chbani, M.; Païs, M. J. Nat. Prod. 1993, 1, 99-104.
6. 5. (a) Wanner, M. J.; Velzel, A. W.; Koomen, G.-J. J. Chem. Soc. Chem. Commun. 1993, 174-175.
7. (b) Burm, B. E. A.; Meijler, M. M.; Korver, J.; Wanner, M. J.; Koomen, G.-J. submitted for publication.
8. 6. (a) Pictet, A.; Spengler, T. Ber. Disch. Chem. Ges. 1911, 44, 2030-2036.
9. See for a recent review: (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842.
10. 7. (a) Gharagozloo, P.; Miyauchi, M.; Birdsall, N. J. M. Tetrahedron, 1996, 52, 10185-10192.
11. (b) Freter, K.; J. Org. Chem., 1975, 40, 2525-2529.
12. (c) Gharat, L. A.; Martin, A. R. J. Het. Chem., 1996, 33, 197-201.
13. (d) Zheng, Q.; Yang, Y.; Martin, A. R. Heterocycles 1994, 37, 1761-1772.
14. 8. (a) Krogsgaard-Larsen, P.; Hjeds, H. Acta Chem. Scand. 1976, B 30, 884-888.
15. (b) Schirmann, P. J.; Matthews, R. S.; Dittmer, D. C. J. Org. Chem. 1983, 48, 4426-4427.
16. 9. 1-alkyl-2,3,4,5,6,1 I-hexahydro-2,6-methano-IH-azocino[3,4-b]indol (for n = 3).
17. 13. (Equation Presented)
18. 11. Wanner, M. J.; Koomen, G.-J. J. Org. Chem. 1995, 60, 5634-5637.
19. 12. Cheng, E.; Botzem, J.; Wanner, M. J.; Burm, B. E. A.; Koomen, G.-J. Tetrahedron 1996, 52, 6725-6732.