Acid-Catalysed epimerization of indolo[2,3-a]quinolizidines 1-, 2- and 3-monosubstituted alkyl derivatives

Tetrahedron

Volumn 53, Issue 14, 1997, Pages 5349-5356

  Lounasmaa, Mauri ^a   Miikki, Lars ^a   Tolvanen, Arto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLIZIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; THERMODYNAMICS;

EID: 0030972668     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00197-X     Document Type: Article

References (33)

1. See, e.g., Monoterpenoid Indole Alkaloids (Saxton, J. E., Ed.), Supplement to Vol. 25, Part 4, Wiley, Chichester, 1994.
2. Le Men, J.; Taylor, W. I., Experientia 1965, 21, 508-510.
3. Cookson, R. C., Chem. Ind. (London) 1953, 337-340. See also Wenkert, E.; Liu, L. H., Experientia 1955, 11, 302-303.
4. Cookson, R. C., Chem. Ind. (London) 1953, 337-340. See also Wenkert, E.; Liu, L. H., Experientia 1955, 11, 302-303.
5. Gaskell, A. J.; Joule, J. A., Tetrahedron 1967, 23, 4053-4063 and references therein.
6. MacPhillamy, H. B.; Dorfman, L.; Huebner, C. F.; Schlittler, E.; St. André, A. F., J. Am. Chem. Soc. 1955, 77, 1071-1072.
7. Cox, E. D.; Cook, J. M., Chem. Rev. 1995, 95, 1797-1842.
8. Whaley, W. M.; Govindachari, T. R., Org. React. 1951, 6, 151-190.
9. Paquette, L. A., Principles of Modern Heterocyclic Chemistry, W. A. Benjamin, Inc., New York, 1968, pp. 284-286.
10. Lounasmaa, M.; Miikki, L.; Tolvanen, A., Tetrahedron 1996, 52, 9925-9930.
11. Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H., J. Org. Chem. 1990, 55, 3068-3074.
12. (a) Din Belle, D.; Tolvanen, A.; Lounasmaa, M., Tetrahedron 1996, 52, 11361-11378;
13. (b) Lounasmaa, M.; Karinen, K.; Din Belle, D.; Tolvanen, A., Tetrahedron Lett. 1996, 37, 1513-1516.
14. Lounasmaa, M.; Karvinen, E., Tetrahedron 1991, 47, 6371-6380.
15. Rosentreter, U.; Born, L.; Kurz, J., J. Org. Chem. 1986, 51, 1165-1171.
16. Wenkert, E.; Moeller, P. D. R.; Shi, Y.-J., J. Org. Chem. 1988, 53, 2383-2386.
17. Lounasmaa, M.; Jokela, R.; Tamminen, T., Heterocycles 1985, 23, 1367-1371.
18. Compound 6 is not mentioned in the literature. Compound 10 has CA registry number 34159-92-7, but no references are given.
19. Chevolot, L.; Husson, H.-P.; Potier, P., Tetrahedron 1975, 31, 2491-2494.
20. (a) Gribble, G. W.; Nelson, R. B., J. Org. Chem. 1973, 38, 2831-2834.
21. (b) Gribble, G. W.; Nelson, R. B.; Johnson J. L.; Levy, G. C., J. Org. Chem. 1975, 40, 3720-3725. See also Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K., J. Am. Chem. Soc. 1976, 98, 3645-3655 (note 55).
22. (b) Gribble, G. W.; Nelson, R. B.; Johnson J. L.; Levy, G. C., J. Org. Chem. 1975, 40, 3720-3725. See also Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K., J. Am. Chem. Soc. 1976, 98, 3645-3655 (note 55).
23. Hoshino, T.; Shimodaira, K., Liebigs Ann. Chem. 1935, 520, 19-30.
24. Potier, P., Rev. Latinoamer. Quim. 1978, 9, 47-54.
25. Lounasmaa, M.; Koskinen, A., Heterocycles 1984, 22, 1591-1612.
26. Grierson, D., Org. React. 1990, 39, 85-295.
27. +) were performed with HyperChemLite™ 1.0 for Windows (Hypercube, Inc.).
28. (a) Cox, E. D.; Li, J.; Hamaker, L. K.; Yu, P.; Cook, J. M., Chem. Commun. 1996, 2477-2478.
29. (b) Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M.; Watson, W. H.; Krawiec, M., J. Org. Chem. 1997, 62, 44-61.
30. Wenkert, E.; Wickberg, B., J. Am. Chem. Soc. 1962, 84, 4914-4919.
31. Jokela, R.; Tamminen, T.; Lounasmaa, M., Heterocycles 1985, 23, 1707-1722.
32. See Ref. 15. See also Jokela, R.; Karvinen, E.; Tolvanen, A.; Lounasmaa, M., Tetrahedron 1988, 44, 2367-2375 (note 15) and Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M., Tetrahedron 1989, 45, 2683-2692 (note 15).
33. See Ref. 15. See also Jokela, R.; Karvinen, E.; Tolvanen, A.; Lounasmaa, M., Tetrahedron 1988, 44, 2367-2375 (note 15) and Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M., Tetrahedron 1989, 45, 2683-2692 (note 15).