Intramolecular acid-catalyzed aldolization of oxindolic methylketones

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2263-2266

  Mirand, Catherine ^a   Papa, Mario ^a   Cartier, Dominique ^a   Lévy, Jean ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031592606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00293-1     Document Type: Article

References (24)

1. 1. a) Cordell, G.A. The Aspidosperma alkaloids. In The Alkaloids; Manske, R.H.F.; Rodrigo, R.G.A. Eds; Academic Press: New York, 1979, 17, pp 199-384.
2. b) Sapi, J.; Massiot, G. The Strychnos Alkaloids. In Indoles. The Monoterpenoid Indole Alkaloids; Saxton, J.E. Ed; John Wiley and Sons : New York, 1994, pp 279-355.
3. 2. For leading references see: a) Oishi, T.; Nagai, M.; Ban, Y. Tetrahedron Lett. 1968, 491-495.
4. b) Ban, Y.; Sendo, Y.; Nagai M.; Oishi, T. Tetrahedron Lett. 1972, 5027-5030.
5. c) Ban, Y.; Sekine, Y.; Oishi, T. Tetrahedron Lett. 1978, 151-154.
6. d) Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880-6881.
7. e) Takano, S.; Shishido, K; Matsuzaka, J.; Sato, M.; Ogasawara, K. Heterocycles 1979, 13, 307-320.
8. f) Doë de Maindreville, M.; Lévy, J. Bull. Soc. Chim. Fr. 1981, II-179-183.
9. g) Vercauteren, J.; Massiot, G.; Lévy, J. J. Org. Chem. 1984, 49, 3230-3231.
10. h) Overman, L.E.; Angle, S.R. J. Org. Chem. 1985, 50, 4021-4028.
11. i) Kuehne, M.E.; Xu, F. J. Org. Chem. 1993, 58, 7490-7497.
12. j) Kuehne, M.E.; Brook, C.S.; Frasier, D.A.; Xu, F. J. Org. Chem. 1994, 59, 5977-5982.
13. k) Benchekroun-Mounir, N.; Dugat, D.; Gramain, J.C., Husson, H.P. J. Org. Chem. 1993, 55, 6457-6465.
14. l) Rawal, V.H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685-2686.
15. 3. a) Laronze, J.Y.; Laronze-Fontaine, J.; Lévy, J.; Le Men, J. Tetrahedron Lett. 1974, 491-494
16. b) Laronze, J.Y.; Cartier, D.; Laronze, J.; Lévy, J. Tetrahedron Lett. 1980, 21, 4441-4444.
17. c) Cartier, D.; Patigny, D.; Lévy, J. Tetrahedron Lett. 1982, 23, 1897-1900.
18. d) Cartier, D.; Ouahrani, M.; Hugel, G.; Lévy, J. Heterocycles 1988, 27, 657-661.
19. e) Cartier, D.; Ouahrani, M.; Lévy, J. Tetrahedron Lett. 1989, 30, 1951-1954.
20. 4. Biogenetic numbering after Le Men, J.; Taylor, W.I. Experientia 1965, 27, 508-511.
21. 5. Cartier, D.; Lévy, J. Tetrahedron 1990, 46, 5295-5304.
22. 6. Lüthy, C.; Konstantin, P.; Untch, K.G. J. Am. Chem. Soc. 1978, 100, 6211-6217.
23. +.), 244, 167, 159, 123.
24. 8. For an example of intramolecular acylation induced by TsOH, see Fu, X.; Kubiak, G.; Zhang, W.; Han, W.; Gupta, A.K.; Cook, J.M. Tetrahedron 1993, 49, 1511-1524.