The first total synthesis of bufobutanoic acid by two routes based on nucleophilic substitution reaction on indole nucleus

Heterocycles

Volumn 53, Issue 5, 2000, Pages 1017-1019

  Kurauchi, Takashi ^a   Nagahama, Yoshiyuki ^a   Hasegawa, Masakazu ^a   Yamada, Koji ^a   Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUFOBUTANOIC ACID; CYTOTOXIC AGENT; INDOLE DERIVATIVE; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0034194821     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-00-8870     Document Type: Article

References (22)

1. This is Part 96 of a series entitled "The Chemistry of Indoles". Part 95: M. Somei, K. Noguchi, R. Yamagami, Y. Kawada, K. Yamada, and F. Yamada, Heterocycles, 2000, 53, 7. All new compounds gave satisfactory spectral and elemental analysis or high-resolution MS data for crystals or gums, respectively. 1b, gum; 4a, gum; 4b, gum; 4c, gum; 5, mp 97.5-99.5°C 6, mp 145-147°C; 7, mp 118-120°C; 8, mp 74-75°C; 9a, mp 151.5-153.5°C.
2. Y. Kamano, H. Morita, R. Takano, A. Kotake, T. Nogawa, H. Hashima, K. Takeya, H. Itokawa, and G. R. Pettit, Heterocycles, 1999, 50, 499.
3. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
4. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
5. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
6. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
7. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
8. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
9. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
10. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
11. K. Nakagawa and M. Somei, Heterocycles, 1991, 32, 873; F. Yamada, K. Kobayashi, A. Shimizu, N. Aoki, and M. Somei, ibid., 1993, 36, 2783; F. Yamada, S. Hamabuchi, A. Shimizu, and M. Somei, ibid., 1995, 41, 1905; M. Somei, Y. Fukui, and M. Hasegawa, ibid., 1995, 41, 2157; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, ibid., 1996, 43, 1855; M. Somei, F. Yamada, T. Izumi, and M. Nakajou, ibid., 1997, 45, 2327; F. Yamada, M. Tamura, and M. Somei, ibid., 1998, 49, 451; M. Somei, N. Oshikiri, M. Hasegawa, and F. Yamada, ibid., 1999, 51, 1237. See also reference 11.
12. Review: M. Somei, Heterocycles, 1999, 50, 1157 and references cited therein.
13. M. Somei, K. Yamada, M. Hasegawa, M. Tabata, Y. Nagahama, H. Morikawa, and F. Yamada, Heterocycles, 1996, 43, 1855.
14. M. Somei, K. Kobayashi, K. Tanii, T. Mochizuki, Y. Kawada, and Y. Fukui, Heterocycles, 1995, 40, 119.
15. Although hydrochloride of 5 is commercially available from Sigma, it is expensive and therefore not suitable as a common starting material for multi-gram scale production of serotonin congeners. Our present method seems to be better to obtain 5 at cheaper cost compared to the conventional one. Another choice is to utilize serotonin hydrochloride as a starting material.
16. M. Somei, J. Synth. Org. Chem., 1982, 40, 387; M. Somei, Y. Makita, and F. Yamada, The 3rd International Kyoto Conference on New Aspects of Organic Chemistry, Abstracts Papers, Nov., 1985, p. 128; M. Somei, Yakugaku Zasshi, 1988, 108, 361. Originality rate is the result of the following calculation: Originality Rate (%) = 100 x [Number of Newly Developed Steps + 1 ] ÷ [Total Number of Synthetic Steps + 1]
17. M. Somei, J. Synth. Org. Chem., 1982, 40, 387; M. Somei, Y. Makita, and F. Yamada, The 3rd International Kyoto Conference on New Aspects of Organic Chemistry, Abstracts Papers, Nov., 1985, p. 128; M. Somei, Yakugaku Zasshi, 1988, 108, 361. Originality rate is the result of the following calculation: Originality Rate (%) = 100 x [Number of Newly Developed Steps + 1 ] ÷ [Total Number of Synthetic Steps + 1]
18. M. Somei, J. Synth. Org. Chem., 1982, 40, 387; M. Somei, Y. Makita, and F. Yamada, The 3rd International Kyoto Conference on New Aspects of Organic Chemistry, Abstracts Papers, Nov., 1985, p. 128; M. Somei, Yakugaku Zasshi, 1988, 108, 361. Originality rate is the result of the following calculation: Originality Rate (%) = 100 x [Number of Newly Developed Steps + 1 ] ÷ [Total Number of Synthetic Steps + 1]
19. A. E. Lanzilotti, R. Littell, W. J. Fanshawe, T. C. McKenzie, and F. M. Lovell, J. Org. Chem., 1979, 44, 4809.
20. 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.
21. M. Somei, H. Morikawa, K. Yamada, and F. Yamada, Heterocycles, 1998, 48, 1117; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, ibid., 1999, 51, 2815.
22. M. Somei, H. Morikawa, K. Yamada, and F. Yamada, Heterocycles, 1998, 48, 1117; M. Hasegawa, K. Yamada, Y. Nagahama, and M. Somei, ibid., 1999, 51, 2815.