Synthesis of new tetracyclic oxazolocarbazoles as functionalized precursors to antioxidative agents, antiostatins and carbazoquinocins

Heterocycles

Volumn 43, Issue 9, 1996, Pages 1847-1854

  Choshi, Tominari ^a   Fujimoto, Hiroyuki ^a   Sugino, Eiichi ^a   Hibino, Satoshi ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001087974     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7532     Document Type: Article

References (21)

1. (a) B. Halliwell and J. M. C. Gutteridge, Method in Enzymology, 1990, 186, 1.
2. (b) B. Hammond, H. A. Kontos, and M. L. Hess, Can. J. Physiol. Pharmacol., 1985, 63, 173.
3. (c) P. A. Cerutti, Science, 1985, 227, 375.
4. (d) D. W. Choi, J. Neurosci., 1990, 10, 2493.
5. (e) H. Kinouchi, C. J. Epstein, T. Mizui, E. Carlson, S. F. Chen, and P. H. Chan, Proc. Natl. Acad. Sci. U. S. A., 1991, 88, 11158.
6. (f) J. T. Coyle and P. Puttfarcken, Science, 1993, 262, 689.
7. C. J. Mo, K. Shin-ya, K. Furihata, K. Furihata, S. Shimazu, Y. Hayakawa, and H. Seto, J. Antibiotics, 1990, 43, 1337.
8. M. Tanaka, K. Shin-ya, K. Furihata, and H. Seto, J. Antibiotics, 1995, 48, 326.
9. Total synthesis of carbazoquinocins A and D was reported by K. Shin and K. Ogasawara in the 116th Annual Meeting of Pharmaceutical Society of Japan, Kanazawa, 1996 (March), Abstract, Vol. 2, p.124.
10. S. Kato, H. Kawai, T. Kawasaki, Y. Toda, T. Urata, and Y. Hayakawa, J. Antibiotics, 1989, 42, 1879.
11. T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, and S. Hibino, Tetrahedron Lett., 1996, 37, 2593.
12. 3 (10 g) to give the crude 2-formyl-3-iodoindole (81%, mp 193-194 °C from EtOH); cf. T. Sakamoto, T. Nagano, T. Kondo, and Y. Yamanaka, Chem. Pharm. Bull., 1988, 36, 2248.
13. (a) T. Shono, Y. Matsumura, and K. Tsubata, Org. Synth., 1984, 63, 206.
14. (b) P.-C. Wang, Heterocycles, 1985, 23, 2237.
15. 2Ph) tetracyclic oxazolocarbazole produced together with an unknown compound, but it was difficult to separate these products.
16. E. J. Corey and J. Das, J. Am. Chem. Soc., 1982, 104, 5551.
17. +).
18. +).
19. +).
20. 1H-nmr
21. +).