Synthesis of cystodamine, a pentacyclic aza-aromatic alkaloid

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4441-4442

  Kitahara, Yoshiyasu ^a   Tamura, Fumiyasu ^a   Kubo, Akinori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMER; REACTION ANALYSIS;

BETULACEAE;

EID: 0030900079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00926-X     Document Type: Article

References (12)

1. Review: Molinski, T. F. Chem. Rev., 1993, 93, 1825-1838.
2. Bontemps, N.; Bonnard, I.; Banaigs, B.; Combaut, G.; Francisco, C. Tetrahedron Lett., 1994, 35, 7023-7026.
3. a) Nebois, P.; Barret, R.; Fillion, H. Tetrahedron Lett., 1990, 31, 2569-2572;
4. b) Villacampa, M.; Pérez, J. M.; Avendaño, C.; Menéndez, J. C. Tetrahedron, 1994, 50, 10047-10054;
5. c) Lévesque, S.; Brassard, P. Heterocycles, 1994, 38, 2205-2218.
6. The quinone (1) was prepared from 3-bromo-2,5-dimethoxyaniline (Guay, V.; Brassard, P. J. Heterocycl. Chem., 1987, 24, 1649-1652) via 7-bromo-5,8-dimethoxy-4(1H)-quinolinone using Cassis' method (Cassis, R.; Tapia, R.; Valderrama, J. A. Synth. Commun., 1985, 15, 125-133) in four steps. (Equation Presented)
7. The quinone (1) was prepared from 3-bromo-2,5-dimethoxyaniline (Guay, V.; Brassard, P. J. Heterocycl. Chem., 1987, 24, 1649-1652) via 7-bromo-5,8-dimethoxy-4(1H)-quinolinone using Cassis' method (Cassis, R.; Tapia, R.; Valderrama, J. A. Synth. Commun., 1985, 15, 125-133) in four steps. (Equation Presented)
8. 8).
9. Kitahara, Y.; Tamura, F.; Kubo, A. Chem. Pharm. Bull., 1994, 42, 1363-1364.
10. Schmitz, F. J.; DeGuzman, F. S.; Hossain, M. B.; van der Helm, D. J. Org. Chem., 1991, 56, 804-808.
11. 8).
12. Kitahara, Y.; Nakahara, S.; Yonezawa, T.; Nagatsu, M.; Kubo, A. Heterocycles, 1993, 36, 943-946.