Model construction for the A-B-C ring system of lysergic acid via Vilsmeier-Haack-type cyclization of 1H-indole-4-propanoic acid derivatives

Helvetica Chimica Acta

Volumn 90, Issue 3, 2007, Pages 574-587

  Kurokawa, Masayuki ^a   Watanabe, Toshiko ^a   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL SUBSTRATE; LYSERGIC ACID; OPTICAL PURITY; RING SYSTEM;

AMINO ACIDS; CHIRALITY; CYCLIZATION; DERIVATIVES; REACTION KINETICS;

CARBOXYLIC ACIDS;

1H INDOLE 4 PROPANOIC ACID DERIVATIVE; 3,7,8,9 TETRAHYDRO 6 PHENYLTHIOPYRANO[3,2 E]INDOLIUM TRIFLUOROACETATE; ALPHA (ACETYLAMINO) N,N DIMETHYL 1H INDOLE 4 PROPANAMIDE; INDOLE DERIVATIVE; LYSERGIC ACID; N,N DIMETHYL 1H INDOLE 4 PROPANOIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; PUMMERER REACTION; SYNTHESIS; VILSMEIER HAACK REACTION;

EID: 34250654992     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790058     Document Type: Article

References (29)

1. A. Hofmann, 'Ergot Alkaloids, Pharmacology', Eds. P. F. Spano and M. Trabucchi, Karger, Basel, Switzerland, 1978, Vol. 16, Suppl. 1, p. 1; L. Lemberger, Fed. Proc. 1978, 37, 2176;
2. D. Berde, O. Schild, 'Handbook of Experimental Pharmacology', Springer Verlag, Berlin, Germany, 1978; Vol. 49, p. 1.
3. a) E. A Kornfeld, E. J. Fornefeld, G. B. Kline, M. J. Mann, D. E. Morrison, R. G. Jones, R. B. Woodward, J. Am. Chem. Soc. 1956, 78, 3087;
4. b) M. Julia, F. LeGoffic, J. Igolen, M. Baillarge, Tetrahedron Lett. 1969, 1569;
5. c) V. W. Armstrong, S. Coulton, R. Ramage, Tetrahedron Lett. 1976, 4311;
6. R. Ramage, V. W. Armstrong, S. Coulton, Tetrahedron 1981, 9 (Suppl.), 157;
7. d) W. Oppolzer, E. Francotte, K. Baettig, Helv. Chim. Acta 1981, 64, 478;
8. e) J. Rebek Jr., D. F. Tai, Tetrahedron Lett. 1983, 24, 859;
9. J. Rebek Jr., D. F. Tai, Y. K. Shue, J. Am. Chem. Soc. 1984, 106, 1813;
10. f) T. Kurihara, T. Terada, R. Yoneda, Chem. Pharm. Bull. 1986, 34, 442;
11. T. Kurihara, T. Terada, S. Harusawa, R. Yoneda, Chem. Pharm. Bull. 1987, 35, 4793;
12. g) T. Kiguchi, C. Hashimoto, T. Naito, I. Ninomyia, Heterocycles 1982, 19, 2279;
13. I. Ninomyia, C. Hashimoto, T. Kiguchi, T. Naito, J. Chem. Soc., Perkin Trans. 1 1985, 941;
14. h) S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1988, 29, 3117;
15. i) J. B. Hendrickson, J. Wang, Org. Lett. 2004, 6, 3.
16. I. Moldvai, E. Temesvari-Major, M. Incze, E. Szentirmay, E. Gacs-Baitz, C. Szantay, J. Org. Chem. 2004, 69, 5993;
17. T. Kurokawa, M. Isomura, H. Tokuyama, T. Fukuyama, private communication.
18. K. Hada, T. Watanabe, T. Isobe, T. Ishikawa, J. Am. Chem. Soc. 2001, 123, 7705;
19. T. Haga, T. Ishikawa, Tetrahedron 2005, 61, 2857;
20. W. Disadee, T. Ishikawa, J. Org. Chem. 2005, 70, 9399;
21. W. Disadee, T. Ishikawa, M. Kawahata, K. Yamaguchi, J. Org. Chem. 2006, 71, 6600.
22. a) D. Nedelec, L. Raincy, U.S. Patent No. 4774242, 1988;
23. b) H. Muratake, M. Natsume, Tetrahedron Lett. 1989, 30, 1815;
24. c) G. Spadoni, C. Balsamini, G. Diamantini, B. Di Giacomo, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, V. Lucini, R. Nonno, M. Pannacci, F. Fraschimi, B. M. Stankov, J. Med. Chem. 1997, 40, 1990.
25. P. R. Carlier, P. C.-H. Lam, D. M. Wong, J. Org. Chem. 2002, 67, 6256.
26. H. Ishii, I. S. Chen, S. Ueki, T. Masuda, M. Morita, T. Ishikawa, J. Chem. Soc., Perkin Trans. 1 1987, 2415.
27. T. Saitoh, T. Ichikawa, Y. Horiguchi, J. Toda, T. Sano, Chem. Pharm. Bull. 2001, 49, 979.
28. Y. Yokoyama, M. Takahashi, M. Takashima, Y. Kohno, H. Kobayashi, K. Kataoka, K. Shidori, Y. Murakami, Chem. Pharm. Bull. 1994, 42, 832.
29. T. Isobe, T. Ishikawa, J. Org. Chem. 1999, 64, 6984.