4-Trifloxy-9-SEM-β-carboline: Preparation and synthetic utility

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4564-4568

  Busacca, Carl A ^a   Eriksson, Magnus C ^a   Dong, Yong ^a   Prokopowicz, Anthony S ^a   Salvagno, Annette M ^a   Tschantz, Matt A ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 BENZYL BETA CARBOLINE; 4 DIETHYLAMIDO BETA CARBOLINE; BETA CARBOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DERIVATIZATION; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0033546217     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990316t     Document Type: Article

References (38)

1. (a) Cook, J. M.; Cox, E. D.; Diaz-Arauzo, H.; Huang, Q.; Reddy, M. S.; Ma, C.; Harris, B.; McKernan, R.; Skolnick, P. J. Med. Chem. 1998, 41, 1 (14), 2537.
2. (b) Dodd, R. H.; Batch, A. J. Org. Chem. 1998, 63, 3 (3), 872.
3. (c) Cook, J. M.; Skolnick, P.; Shannon, H. E. Heterocycles 1986, 24 (10), 2845.
4. (d) Cook, J. M.; Cain, M.; Weber, R. W.; Guzman, F.; Barker, S. A.; Rice, K. C.; Crawley, J. N.; Paul, S. M.; Skolnick, P. J. Med. Chem. 1982, 25 (9), 1081.
5. (e) Lippke, K. P.; Schunack, W. G.; Wenning, W.; Muller, W. E. J. Med. Chem. 1983, 26 (4), 499.
6. (a) Kozikowski, A. P.; Chen, Y.-Y. J. Org. Chem. 1981, 46 (25), 5248.
7. (b) Hartman, P. J.; Noland, W. E. J. Am. Chem. Soc. 1954, 76, 3227.
8. (c) Noland, W. E.; Christensen, G. M., Sauer, G. L.; Dutton, G. G. S. J. Am. Chem. Soc. 1955, 77, 456.
9. (d) Lehmann, J.; Jiang, N.; Behncke, A. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 6 (10), 813.
10. (e) Cook, J. M.; Skolnick, P.; McKernan, R.; Cox, E. D.; Diaz-Arauzo, H.; Huang, Q.; Reddy, M. S.; Ma, C.; Harris, B. J. Med. Chem. 1998, 41 (14), 2537.
11. For recent examples, see: (a) Rodriguez, R.; Diez, A.; Rubiralta, M.; Giralt, E. Heterocycles 1996, 43 (3), 513. (b) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. Tetrahedron: Asymmetry 1995, 6 (2), 455.
12. For recent examples, see: (a) Rodriguez, R.; Diez, A.; Rubiralta, M.; Giralt, E. Heterocycles 1996, 43 (3), 513. (b) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. Tetrahedron: Asymmetry 1995, 6 (2), 455.
13. (a) Pandit, U.K.; Hiemstra, H. C.; Bieraugel, H.; Wijnberg, M. Tetrahedron 1983, 39 (23), 3981.
14. (b) Cook, J. M.; Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G. S.; Yamanaka, E.; Hutchins, L.; DiPierro, M. J. Org. Chem. 1979, 44 (4), 535.
15. (a) Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56 (8), 2701.
16. (b) Martin, S. F.; Benage, B.; Hunter, J. E. J. Am. Chem. Soc. 1988, 110 (17), 5925.
17. (a) Cook, J. M.; Campos, O.; DiPierro, M.; Cain, M.; Mantei, R.; Gawish, A. Heterocycles 1980, 14 (7), 975.
18. Corbiere, J. 19 Nov. 1981, D'Invention 81 21650. No. de publication 2, 516, 512.
19. Cook, J. M.; Cain, M.; Mantei, R. J. Org. Chem. 1982, 47 (25), 4933.
20. (a) Bergman, J.; Carlsson, R.; Misztal, S. Acta Chem. Scand. B 1976, 30, 853.
21. (b) Yonemitsu, O.; Oikawa, Y. J. Org. Chem. 1977, 42, 1213.
22. (c) Yonemitsu, O.; Oikawa, Y.; Yoshioka, T.; Mohri, K. Heterocycles 1979, 12 (11), 1457.
23. (d) Yonemitsu, O.; Oikawa, Y.; Yoshioka, T.; Mohri, K. J. Chem. Res. Synth. 1981, 194.
24. (e) Cook, J. M.; Hagen, T. J.; Narayanan, K.; Names, J. J. Org. Chem. 1989, 54 (9), 2170.
25. SEM = Trimethysilylethoxymethyl.
26. For a seven step synthesis of 4-hydroxy-9-benzyl β-carboline by an entirely different route, see: Murakami, Y.; Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y. Tetrahedron 1997, 53 (5), 1593.
27. Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
28. (a) Kumada, M.; Tamao, K.; Sumitani, K. J. Am. Chem. Soc. 1972, 94, 4374.
29. (b) Kumada, M.; Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S-i.; Nakajima, I.; Minato, A. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
30. (c) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
31. Snieckus, V.; Sengupta, S.; Leite, M., Raslan, D. S.; Quesnelle, C. A. J. Org. Chem. 1992, 57, 4066.
32. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
33. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1995, 36 (15), 2615.
34. (a) Muchowski, J. M.; Solas, D. R. J. Org. Chem. 1984, 49, 203-205.
35. (b) Labadie, S. S.; Teng, E. J. Org. Chem. 1994, 59, 4250.
36. Johnstone, R. A. W.; Neil McLean, W. Tetrahedron Lett. 1988, 29, 5553.
37. Frauenrath, H.; Wille, A.; Tomm, S. Synthesis 1998, 305.
38. Rudie, A. W.; Lichtenberg, D. W.; Katcher, M. L.; Davison, A. Inorg. Chem. 1978, 17, 2859-2863.