Transbromination of brominated pyrrole and imidazole derivatives: Synthesis of the C11N5 marine alkaloid stevensine

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8121-8124

  Xu, Ying Zi ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a Department of Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; STEVENSINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030569271     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01888-6     Document Type: Article

References (13)

1. 1. March, J., Advanced Organic Chemistry, 4th ed., March, J., John Wiley and Sons, New York, 1992, p 566.
2. 2. (a) Christophersen, C., The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed; Academic Press, New York, 1985, Vol. 24, p 25.
3. (b) Kobayashi, J.; Ishibashi, M. The Alkaloids, Chemistry and Pharmacology, Brossi, A., Ed; Academic Press, New York, 1992, Vol. 41, p 41.
4. 3. Albizati, K. F.; Faulkner, D. J. J. Org. Chem. 1985, 50, 4163.
5. 4. De Nauteuil, G.; Ahond, A.; Guilhem, J.; Poupat, C.; Tran Huu Pau, E.; Potier, P.; Pusset, M.; Pusset, J.; Laboute, P. Tetrahedron 1985, 41, 6019.
6. 5. Xu, Y.-z.; Phan, G.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1994, 35, 351.
7. 6. Kobayashi, J.; Ohizumi, Y.; Nakamura, H.; Hirata, Y.; Wakamatsu, K.; Miyazawa, T. Experientia 1986, 42, 1064.
8. 3OD) δ 50.4, 99.9, 110.0, 116.0, 121.1, 124.3, 124.5, 125.8, 128.8, 148.6, 163.6.
9. 8. (a) Olah, G. A.; Meyer, M. W. J. Org. Chem. 1962, 27, 3464.
10. (b) Jacquesy, J. C.; Jauannetaud, M. P. Tetrahedron Lett. 1982, 23, 1673.
11. 9. Anderson, H. J.; Lee, S. F. Can. J. Chem., 1956, 43, 409.
12. 10. (a) Cimino, G.; DeRosa, S.; Destefano, S.; Mazzarella, L.; Puliti, R.; Sodano, G. Tetrahedron Lett., 1982 23, 767.
13. (b) Kitagawa, I.; Kobayashi, M.; Kitanaka, K.; Kido, M.; Kyogoku, Y. Chem. Pharm. Bull. 1983, 31, 2321.