Synthesis of 3a-(indol-3-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole core of leptosins D-F based on nucleophilic substitution reaction on indole nucleus

Heterocycles

Volumn 53, Issue 6, 2000, Pages 1255-1258

  Yamada, Fumio ^a   Goto, Aya ^a   Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; LEPTOSIN D; LEPTOSIN E; LEPTOSIN F; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG SYNTHESIS; JAPAN; MOLECULAR INTERACTION;

EID: 0034210264     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-00-8888     Document Type: Article

References (15)

1. This is Part 97 of a series entitled "The Chemistry of Indoles". Part 96: T. Kurauchi, Y. Nagahama, M. Hasegawa, K. Yamada, and M. Somei, Heterocycles, 2000, submitted. All new compounds gave satisfactory spectral and elemental analysis or high-resolution MS data for crystals or gums, respectively. 13, mp 223-225°C (decomp); 14, gum; 15, gum; 16, mp 219.0-220.5°C.
2. H. Minato, M. Matsumoto, and T. Katayama, J. Chem. Soc., Perkin Trans, 1, 1973, 1819.
3. C. Takahashi, A. Numata, Y. Ito, E. Matsumura, H. Iwaki, and K. Kushida, J. Chem. Soc., Perkin Trans. 1, 1994, 1859.
4. D. Crich, E. Fredette, and W. J. Flosi, Heterocycles, 1998, 48, 545.
5. Review: M. Somei, Heterocycles, 1999, 50, 1157 and references cited therein.
6. It is also possible that the elimination of 1-hydroxy group and an attack by nucleophiles follow the concerted mechanism.
7. F. Yamada, D. Shinmyo, and M. Somei, Heterocycles, 1994, 38, 273 and see the reference 2 in the report; M. Somei, H. Morikawa, K. Yamada, and F. Yamada, ibid., 1998, 48, 1117; J. A Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815.
8. F. Yamada, D. Shinmyo, and M. Somei, Heterocycles, 1994, 38, 273 and see the reference 2 in the report; M. Somei, H. Morikawa, K. Yamada, and F. Yamada, ibid., 1998, 48, 1117; J. A Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815.
9. F. Yamada, D. Shinmyo, and M. Somei, Heterocycles, 1994, 38, 273 and see the reference 2 in the report; M. Somei, H. Morikawa, K. Yamada, and F. Yamada, ibid., 1998, 48, 1117; J. A Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815.
10. F. Yamada, D. Shinmyo, and M. Somei, Heterocycles, 1994, 38, 273 and see the reference 2 in the report; M. Somei, H. Morikawa, K. Yamada, and F. Yamada, ibid., 1998, 48, 1117; J. A Joule, "Progress in Heterocyclic Chemistry", Vol. 11, ed. by G. W. Gribble and T. L. Gilchrist, Elsevier Science Ltd., Oxford, 1999, pp. 45-65; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, Heterocycles, 1999, 51, 2815.
11. M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, Heterocycles, 1999, 51, 1237.
12. M. Hasegawa, Y. Nagahama, K. Kobayashi, M. Hayashi, and M. Somei, Heterocycles, 2000, 52, 483.
13. M. Somei, K. Kobayashi, K. Tanii, T. Mochizuki, Y. Kawada, and Y. Fukui, Heterocycles, 1995, 40, 119.
14. Formation of 12 could involve 3-Nb-trifluoroacetylaminoethyl-3-mesyloxy-3H-indole as an unstable intermediate. Isolation of a stable indolenine intermediate: P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749.
15. M. Somei, T. Kawasaki, K. Shimizu, Y. Fukui, and T. Ohta, Chem. Pharm. Bull., 1991, 39, 1905.