Enediynes as antitumor compounds: Synthesis of tetrahydropyridine derivatives

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1369-1371

  Braña, Miguel F ^a   Morán, Marina ^a   De Vega, María Jesús Pérez ^a   Pita Romero, Isabel ^a  

^a Laboratorios Knoll SA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMENAFIDE; ANTINEOPLASTIC AGENT; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLON CANCER; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL;

EID: 0029939314     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951188l     Document Type: Article

References (29)

1. For a review see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed, Engl. 1991, 30, 1387. (b) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. (c) Nicolaou, K. C.; Smith, A. L.; Yue E. W. Proc. Natl. Acad. Sci. U.SA. 1993, 90, 5881 and references tnerein.
2. For a review see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed, Engl. 1991, 30, 1387. (b) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. (c) Nicolaou, K. C.; Smith, A. L.; Yue E. W. Proc. Natl. Acad. Sci. U.SA. 1993, 90, 5881 and references tnerein.
3. For a review see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed, Engl. 1991, 30, 1387. (b) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172. (c) Nicolaou, K. C.; Smith, A. L.; Yue E. W. Proc. Natl. Acad. Sci. U.SA. 1993, 90, 5881 and references tnerein.
4. (a) Bergman, R. G. Acc. Chem. Res. 1973, 6, 25.
5. (b) Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660.
6. (c) Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J. Am. Chem. Soc 1981, 103, 4082.
7. (d) Lockhart, T. P ; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091.
8. Kadow, J. F.; Cook, D. J.; Doyle, T. W.; Langley, D. R.; Pham, K. M.; Vyas, D. M.; Wittman, M. D. Tetrahedron 1994, 50, 1519.
9. (a) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657.
10. (b) Yoon, T.; Shair, M. D.; Danishefsky, S. J.; Shulte, G. K. J. Org. Chem. 1994, 59, 3752.
11. (c) Maier, M. E.; Abel, U. Synlett 1995, 38.
12. (a) Porco J. A., Jr.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410.
13. (b) Wender, P. A.; Zercher, C. K.; Beckhman, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
14. (c) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449.
15. Brana, M. F.; Morán, M.; Pérez de Vega, M. J.; Pita-Romero, I. Tetrahedron Lett. 1994, 35, 8655.
16. Burke, H. M.; Joullie, M. M. J. Med Chem. 1978, 21, 1084.
17. (a) Braña, M. F.; Castellano, J. M.; Jiménez, A.; Llombart, A.; Rabadán, F. P.; Roldán, C. M.; Roldán, C.; Santos, A.; Vázquez, D. Curr. Chemother. 1978, 1216.
18. (b) Braña, M. F; Sanz, A. M.; Castellano, J. M.; Roldán, C. M.; Roldán, C. Eur. J. Med. Chem. (Chim. Therapeutica) 1981, 16, 207.
19. Yamaguchi, R.; Nakazono,Y.; Kawanishi, M. Tetrahedron Lett. 1983, 24, 1801.
20. Lazar, L.; Fueloep, F.; Dombi, G.; Bernath, G.; Argay, G.; Kalman, A. Hung. Magy. Kem. Foly. 1990, 36, 349.
21. Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217.
22. (a) Stephans, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
23. (b) Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1981, 22, 310.
24. (c) Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1985, 26, 3811.
25. Wender, P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311.
26. Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271.
27. 4. The performance of several experiments did not lead to the unambiguous determination of the structure. However, study of the cyclized derivative 15 allowed us the full assignment of the structure of aldehyde (Z)-13.
28. Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
29. Mitsunobu, O. Synthesis 1981, 1.