Regiospecific Bromination of 3-Methylindoles with NBS and Its Application to the Concise Synthesis of Optically Active Unusual Tryptophans Present in Marine Cyclic Peptides

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7447-7456

  Liu, Ruiyan ^a   Zhang, Puwen ^a   Gan, Tong ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001606083     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971067g     Document Type: Article

References (38)

1. This study was reported in preliminary form in the following: (a) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 3103. (b) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 7411. (c) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 9133.
2. This study was reported in preliminary form in the following: (a) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 3103. (b) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 7411. (c) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 9133.
3. This study was reported in preliminary form in the following: (a) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 3103. (b) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 7411. (c) Zhang. P; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 9133.
4. Pelletier, S. W. Chemistry of the Alkaloids; Van Nostrand Reinhold Book Corporation: New York, 1970.
5. Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975; Vols. I-III.
6. Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753.
7. Braekman, J. C.; Daloze, D.; Moussiaux, B. J. Nat. Prod. 1987, 50, 994.
8. Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Am. Chem. Soc. 1991, 113, 7811.
9. Kobayashi, J.; Sato, M.; Murayama, T.; Ishibashi, M.; Wälchi, M. R.; Kanai, M.; Shoji, J.; Ohizumi, Y. J. Chem. Soc., Chem. Commun. 1991, 1050.
10. Kobayashi, J.; Itagaki, F.; Shigemori, H.; Ishibashi, M.; Takahashi, K.; Ogura, M.; Nagasawa, S.; Nakamura, T.; Hirota, H.; Ohta, T.; Nozoe, S. J. Am. Chem. Soc. 1991, 113, 7812.
11. Kobayashi, J.; Itagaki, F.; Shigemori, H.; Takao, T.; Shimonishi, Y. Tetrahedron 1995, 51, 2525.
12. Hidaka, H.; Yamaki, T.; Totsuka, T.; Asano, M. Mol. Pharmacol. 1978, 15, 55.
13. Inman, W.; Crews, P. J. Am. Chem. Soc. 1989, 111, 2822.
14. Kobayashi, J.; Sato, M.; Ishibashi, M.; Shigemori, H.; Nakamura, T.; Ohizumi, Y. J. Chem. Soc., Perkin Trans. 1 1991, 2609.
15. Ishibashi, M.; Li, Y.; Sato, M.; Kobayashi, J. Nat. Prod. Lett. 1994, 4, 293.
16. Zhang, L. H.; Cook, J. M. J. Am. Chem. Soc. 1990, 112, 4088.
17. Fu, X.; Cook, J. M. J. Am. Chem. Soc. 1992, 114, 6910.
18. Bi, Y.; Zhang, L. H.; Hamaker, L. K.; Cook, J. M. J. Am. Chem. Soc. 1994, 116, 9027.
19. Hamaker, L. K.; Cook, J. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier Science: Amsterdam, 1995; Vol. 9, p 23.
20. Bi, Y.; Hamaker, L. K.; Cook, J. M. In Studies in Natural Products Chemistry, Bioactive Natural Products, Part A; Basha, F. Z., Rahman, A., Eds.; Elsevier Science: Amsterdam, 1993; Vol. 13, p 383.
21. Ashworth, P.; Broadbelt, B.; Jankowski, P.; Kocienski, P.; Pimm, A.; Bell, R. Synthesis 1995, 199.
22. Schmidt, U.; Weinbrenner, S. Synthesis 1996, 28.
23. Grieco, P. A.; Hon, Y. S.; Perez-Medrano, A. J. Am. Chem. Soc. 1988, 110, 1630.
24. Chu, K. S.; Negrete, G. R.; Konopelsky, J. P. J. Am. Chem. Soc. 1991, 56, 1993.
25. Rao, R.; Gujar, M. K.; Nallagandu, B. R.; Bhandari, A. Tetrahedron Lett. 1993, 34, 7085.
26. Phillips, R. S.; Cohen, L. A. J. Am. Chem. Soc. 1988, 106, 2023.
27. Schöllkopf, U.; Lonsky, R.; Lehr, P. Liebigs Ann. Chem. 1985, 413.
28. Zhang, P.; Cook, J. M. Synth. Commun. 1995, 25, 3883.
29. Gruter, G. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473 and references cited therein.
30. Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374.
31. Abramovitch, R. A.; Shapiro, D. S. J. Chem. Soc. 1956, 4589.
32. Nagarathnam, D.; Johnson, M. E. Synth. Commun. 1993, 23, 2011.
33. Sevricourt, M. C. d.; Robba, M. Bull. Soc. Chim. Fr. 1977, 139.
34. Gilchrist, T. L. Heterocyclic Chemistry; John Wiley & Sons Inc.: New York, 1985; p 161.
35. Porter, J.; Dykert, J.; Rivier, J. Int. J. Peptide Protein Res. 1987, 30, 13.
36. Liu, R. Ph.D. Thesis, University of Wisconsin-Milwaukee, 1996.
37. Fleming, I.; Woolias, M. J. Chem. Soc., Perkin Trans. 1 1979, 829.
38. Hamaker, L. K. Ph.D. Thesis, University of Wisconsin-Milwaukee, 1995.