A novel synthetic method of pyrrolo[2,3-b]indoles and its application to the synthesis of (±)-debromoflustramine B1

Heterocycles

Volumn 45, Issue 12, 1997, Pages 2327-2330

  Somei, Masanori ^a   Yamada, Fumio ^a   Izumi, Tomoyuki ^a   Nakajou, Masahiro ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000429940     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-97-7989     Document Type: Article

References (25)

1. Nucleophilic substitution reactions were suggested in the following reports: R. J. Sundberg, J. Org. Chem., 1965, 30, 3604;
2. J. Billet and S. G. Smith, Tetrahedron Lett, 1969, 4465;
3. P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749;
4. T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350;
5. M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639;
6. D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589;
7. M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem., 1981, 46, 2054;
8. M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008;
9. M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, J. Chem. Soc., Perkin Trans. ibid., 1982, 435;
10. L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, J. Chem. Soc., Perkin Trans. ibid., 1983, 2417;
11. T. Nagayoshi, S. Saeki, and M. Hamana, Chem. Pharm. Bull, 1984, 32, 3678;
12. R. M. Acheson, "Advances in Heterocyclic Chemistry", Vol. 51, Academic Press, Inc., New York, pp. 105-175, 1990 ;
13. J. Becher, P. L. Jfrgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127;
14. P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, J. Org. Chem. ibid., 1992, 57, 3881.
15. a) Review: M. Somei, J. Synth. Org. Chem., 1991, 49, 205.
16. b) T. Kawasaki, A. Kodama, T. Nishida, K. Shimizu, and M. Somei, Heterocycles, 1991, 32, 221;
17. c) M. Somei, T. Kawasaki, Y. Fukui, F. Yamada, T. Kobayashi, H. Aoyama, and D. Shinmyo, Heterocycles ibid., 1992, 34, 1877;
18. d) F. Yamada, Y. Fukui, D. Shinmyo, and M. Somei, Heterocycles ibid., 1993, 35, 99;
19. e) M. Somei and Y. Fukui, Heterocycles ibid., 1993, 36, 1859;
20. f) F. Yamada, D. Shinmyo, and M. Somei, Heterocycles ibid., 1994, 38, 273.
21. M. F. Comber and C. J. Moody, Synthesis, 1992, 731.
22. Chromium complex: A. P. Kozikowski and K. Isobe, J. Chem. Soc., Chem. Commun., 1978, 1076;
23. M. F. Semmelhack, W. Wulff, and J. L. Garcia, J. Organomet. Chem., 1982, 240, C5;
24. C. W. Holzapfel and F. W. H. Kruger, Aust. J. Chem., 1992, 45, 99;
25. M. F. Semmelhack and H. Rhee, Tetrahedron Lett, 1993, 34, 1399 and references cited therein.