Synthesis of 4,5-disubstituted benzo[c][2,7]naphthyridines by combined metalation-palladium-catalysed cross-coupling strategies. Preparation of 8H-pyrido[4,3,2-mn]acridone as a model of cystodytin alkaloids

Synthetic Communications

Volumn 26, Issue 23, 1996, Pages 4421-4436

  Guillier, F ^a   Nivoliers, F ^a   Cochennec, C ^a   Godard, A ^a   Marsais, F ^a   Queguiner G ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; ALKALOID; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029847857     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003845     Document Type: Article

References (23)

1. For recent review of these alkaloids, see : a) Davidson, B.S. Chem. Rev., 1993, 93, 1771. b) Molinski, T.F. Chem. Rev., 1993, 93, 1825. c) Salas, M.; Alvarez, M.; Joule, J.A. Heterocycles, 1991, 32, 759. d) Alvarez, M.; Joule, J.A. Heterocycles, 1992, 34, 2385.
2. For recent review of these alkaloids, see : a) Davidson, B.S. Chem. Rev., 1993, 93, 1771. b) Molinski, T.F. Chem. Rev., 1993, 93, 1825. c) Salas, M.; Alvarez, M.; Joule, J.A. Heterocycles, 1991, 32, 759. d) Alvarez, M.; Joule, J.A. Heterocycles, 1992, 34, 2385.
3. For recent review of these alkaloids, see : a) Davidson, B.S. Chem. Rev., 1993, 93, 1771. b) Molinski, T.F. Chem. Rev., 1993, 93, 1825. c) Salas, M.; Alvarez, M.; Joule, J.A. Heterocycles, 1991, 32, 759. d) Alvarez, M.; Joule, J.A. Heterocycles, 1992, 34, 2385.
4. For recent review of these alkaloids, see : a) Davidson, B.S. Chem. Rev., 1993, 93, 1771. b) Molinski, T.F. Chem. Rev., 1993, 93, 1825. c) Salas, M.; Alvarez, M.; Joule, J.A. Heterocycles, 1991, 32, 759. d) Alvarez, M.; Joule, J.A. Heterocycles, 1992, 34, 2385.
5. Schmitz, F.J.; Agarwal, S.K.; Gunasekara, S.P.; Schmidt, P.G.; Schoolery, J.N. J. Am. Chem. Soc., 1983, 105, 4835.
6. a) Kobayashi, J.; Cheng, J.; Walchli, M. R.; Nakamura, H.; Yoshimasa, H.; Takuma, S.; Ohizumi; Y. J. Org. Chem., 1988, 53, 1800.
7. b) Kobayashi, J.; Tsuda, M.; Tanabe, A.; Ishibashi, M.; Cheng, J.; Yamamura, S.; Sasaki, T. J. Nat. Prod., 1991, 54, 1634.
8. Moody, C.J.; Thomas, R. Heterocycl. Nat. Prod. Synth., 1992, 2, 377.
9. Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Advances in Heterocyclic Chemistry, 1991, 52, 187.
10. Godard, A.; Marsais, F.; Plé, N.; Trecourt, F.; Turck, A.; Quéguiner, G. Heterocycles, 1995, 40, 1055.
11. a) Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem., 1993, 58, 7832.
12. b) Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G. Tetrahedron Lett., 1994, 35, 6489.
13. c) Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G.; Siddiqui, M.A.; Snieckus, V. J. Org. Chem., 1995, 60, 292.
14. Walters, M.A.; Shay, J.J. Tetrahedron Lett., 1995, 36, 7575.
15. Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron, 1993, 49, 49.
16. Cochennec, C.; Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. J. Chem. Soc. Perkin Trans. I, 1995, 979.
17. a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun., 1981, 11, 513.
18. b) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc., 1989, 111, 314.
19. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett., 1992, 207.
20. Kosugi, M.; Sumiya, T.; Obara Y.; Suzuki, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1987, 60, 767.
21. Bizot, J. Bull. Soc. Chim. Fr., 1967, 1, 15.
22. Coulsen, D.R. Inorg. Syn., 1972, 13, 121.
23. Soderquist, J.A.; Hsu, G.I. Organometallics, 1982, 1, 830.