Stereoselective synthesis of methyl 3α-ethyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine- 1α-carboxylate: A key intermediate for the preparation of tacamine-type indole alkaloids

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1513-1516

  Lounasmaa, Mauri ^a   Karinen, Kimmo ^a   Din Belle, David ^a   Tolvanen, Arto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; QUINOLIZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029935579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00052-4     Document Type: Article

References (27)

1. Lounasmaa, M.; Tolvanen, A. The Eburnamine-Vincamine Alkaloids. In The Alkaloids; Cordell, G. A. Ed., Academic Press, New York, 1992, vol. 42, pp. 1-116.
2. (a) van Beek, T. A.; Lankhorst, P. P.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron Lett., 1982, 23, 4827-4830;
3. (b) van Beek, T. A.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron, 1984, 40, 737-748.
4. Syntheses of tacamine (1): (a) (partial) Le Men, J.; Caron-Sigaut, C.; Hugel, G.; Le Men-Olivier, L.; Lévy, J. Helv. Chim. Acta, 1978, 61, 566-570;
5. (b) Szabó, L.; Márványos, E.; Tóth, G.; Szántay, Jr., Cs.; Kalaus, Gy.; Szántay, Cs. Heterocycles, 1986, 24, 1517-1525;
6. (c) Lounasmaa, M.; Din Belle, D; Tolvanen, A. Tetrahedron Lett., 1994, 35, 6151-6154.
7. Syntheses of tacamonine (pseudovincamone): (a) Massiot, G.; Sousa Oliveira, F.; Lévy, J. Bull. Soc. Chim. Fr. II, 1982, 185-190,
8. (b) Ihara, M.; Setsu, F.; Shohda, M.; Taniguchi, N.; Fukumoto, K. Heterocycles, 1994, 37, 289-292;
9. (c) Ihara, M.; Setsu, F.; Shohda, M.; Taniguchi, N.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem., 1994, 59, 5317-5323;
10. (d) Lounasmaa, M.; Din Belle, D.; Tolvanen, A. Tetrahedron Lett., 1995, 36, 7141-7144.
11. Tolvanen, A.; Din Belle, D.; Lounasmaa, M. Helv. Chim. Acta, 1994, 77, 709-715.
12. Lounasmaa, M.; Din Belle, D.; Tolvanen, A. Liebigs Ann., 1995, 1385-1387.
13. This pyridine is actually a natural product: (a) McLean, S.; Murray, D. G. Can. J. Chem., 1972, 50, 1478-1485;
14. (b) Delaude, C.; Thépenier, P.; Jacquier, M.-J.; Massiot, G.; Le Men-Olivier, L. Bull. Soc. R. Sci. Liege, 1992, 61, 429-440;
15. (c) Bruix, M.; Rumbero, A.; Vázquez, P. Photochemistry, 1993, 33, 1257-1261. See also: Bracher, F.; Papke, T. Monatsh. Chem., 1995, 126, 805-809.
16. (c) Bruix, M.; Rumbero, A.; Vázquez, P. Photochemistry, 1993, 33, 1257-1261. See also: Bracher, F.; Papke, T. Monatsh. Chem., 1995, 126, 805-809.
17. Jokela, R.; Tamminen, T.; Lounasmaa, M. Heterocycles, 1985, 1707-1722.
18. 3): 169.5 and 169.4 (C=O), 69.4 and 68.6 (-C(OH)Me), 21.2 and 20.0 (-C(OH)Me).
19. 3): 177.7 (C=O), 72.7 (-CH(OH)Me), 21.0 (-CH(OH)Me).
20. 3): 177.6 (C=O), 72.2 (-CH(OH)Me), 23.5 (-CH(OH)Me).
21. 3): 177.0 (C=O), 120.4 (= CHMe), 12.7 (=CHMe).
22. 3): 176.8 (C=O), 120.2 (= CHMe), 12.8 (=CHMe).
23. 3): 173.7 (C=O), 120.4 (= CHMe), 12.7 (=CHMe).
24. 3): 174.4 (C=O), 119.8 (= CHMe), 12.9 (=CHMe).
25. Lounasmaa, M.; Jokela, R.; Hanhinen, P.; Miettinen, J.; Salo, J. Tetrahedron, 1994, 50, 9207-9222.
26. 3).
27. For a very recent approach, see Ihara, M.; Ishida, Y.; Tokunaga, Y.; Kabuto, C.; Fukumoto, K. J. Chem. Soc., Chem. Commun., 1995, 2085-2086.