Synthesis of homofascaplysin C and indolo[2,3-a]carbazole from ditryptophans

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8537-8545

  Carter, David S ^a   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FASCAPLYSIN; IMINE; INDOLE DERIVATIVE; PEPTIDE; TRYPTOPHAN DERIVATIVE;

ALKYLATION; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL STRUCTURE; CROSS LINKING; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033550168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909249     Document Type: Article

References (32)

1. Bergman, J.; Koch, E.; Pelcman, B. Tetrahedron 1995, 51, 5631.
2. Gribble, G. W.; Berthel, S. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers: Dordrecht, 1993; Vol. 12.
3. Gillner, M.; Bergman, J.; Cambillau, C.; Alexandersson, M.; Fernstrom, B.; Gustafsson, J. A. Mol. Pharm. 1993, 44, 336.
4. Pierce, C. J.; Doyle, T. W.; Forenza, S.; Lam, K. S.; Schroeder, D. R. J. Nat. Prod. 1988, 51, 937.
5. Gribble, G. W.; Pelcman, B. J. Org. Chem. 1992, 57, 3636.
6. Dubovitskii, S. V. Tetrahedron Lett. 1996, 37, 5207.
7. Roll, D. M.; Ireland, C. M.; Lu, H. S. M.; Clardy, J. J. Org. Chem. 1988, 53, 3276.
8. Jimenez, C.; Quinoa, E.; Adamczeski, M.; Hunter, L. M.; Crews, P. J. Org. Chem. 1991, 56, 3403.
9. Sasaki, T.; Ohtani, I. I.; Tanaka, J.; Higa, T. Tetrahedron Lett. 1999, 40, 303.
10. Omori, Y.; Matsuda, Y.; Aimoto, S.; Shimonishi, Y.; Yamamoto, M. Chem. Lett. 1976, 805.
11. Stachel, S. J.; Habeeb, R. L.; Van Vranken, D. L. J. Am. Chem. Soc. 1996, 118, 1225.
12. Carter, D. S.; Van Vranken, D. L. Tetrahedron Lett. 1996, 37, 5629.
13. Slates, H. L.; Taub, D.; Kuo, C. H.; Wendler, N. L. J. Org. Chem. 1964, 29, 1424.
14. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
15. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979.
16. Ogibin, Y. N.; Katzin, M. I.; Nikishin, G. I. Synthesis 1974, 889.
17. Kosugi, Y.; Hamaguchi, H.; Nagasaka, T.; Ozawa, N.; Ohki, S. Heterocycles 1980, 14, 1245.
18. Wieland, T.; Fritz, H. Chem. Ber. 1953, 86, 1186.
19. Riniker, B.; Schwyzer, R. Helv. Chim. Acta 1964, 47, 2375.
20. Kawasaki, K.; Maeda, M.; Watanabe, J.; Kaneto, H. Chem. Pharm. Bull. 1988, 36, 1766.
21. Rafelson, M. E.; Ehrensvärd, G.; Bashford, M.; Saluste, E.; Hadén, K. G. J. Biol. Chem. 1954, 211, 725.
22. Gilbert, E. J.; Ziller, J. W.; Van Vranken, D. L. Tetrahedron 1997, 53, 16553.
23. Macromodel v. 6.5.
24. Hashizume, K.; Shimonishi, Y. Bull. Chem. Soc. Jpn. 1981, 54, 3806.
25. Yan, Y.; Tropsha, A.; Hermans, J.; Erickson, B. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7898.
26. Suvorov, N. N.; Preobrazhenskaya, M. N. Zh. Obsch. Khim. 1961, 31, 2839.
27. Miniker, T. D.; Mukhanov, V. I.; Chkanikov, N. D.; Yartzeva, I. V.; Preobrazhenskaya, M. N. Carbohydr. Res. 1978, 64, 17.
28. Chisholm, J. D.; Van Vranken, D. L. J. Org. Chem. 1995, 60, 6672.
29. Okey, A. B.; Riddick, D. S.; Harper, P. A. Trends Pharm. Sci. 1994, 15, 226.
30. Gillner, M.; Bergman, J.; Cambillau, C.; Fernstrom, B.; Gustafsson, J. A. Mol. Pharm. 1993, 28, 357.
31. Rannug, U.; Rannug, A.; Sjöberg, U.; Li, H.; Westerholm, R.; Bergman, J. Curr. Biol. 1995, 2, 841.
32. Gilbert, E. J.; Van Vranken, D. L. J. Am. Chem. Soc. 1996, 118, 5500.