Sponge's molecular diversity through the ambivalent reactivity of 2-aminoimidazole: A universal chemical pathway to the oroidin-based pyrrole-imidazole alkaloids and their palau'amine congeners

European Journal of Organic Chemistry

Volumn , Issue 2, 2001, Pages 237-243

  Mourabit, Ali Al ^a   Potier, Pierre ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

2 Aminoimidazole; Alkaloids; Biogenetic pathway; Marine natural products; Metabolism; Palau'amine

Indexed keywords

2 AMINOIMIDAZOLE; IMIDAZOLE DERIVATIVE; NATURAL PRODUCT; OROIDIN; PALAU'AMINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ACANTHELLA; AGELAS; ARTICLE; AXINELLA; BIODIVERSITY; CHEMICAL ANALYSIS; DRUG BINDING; ENZYME MECHANISM; HYMENIACIDON; MOLECULAR BIOLOGY; PHAKELIA; REACTION ANALYSIS; SPECIES DIFFERENCE; SPONGE (PORIFERA); SYNTHESIS;

EID: 0035136516     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. [1a] R. B. Kinnel, H.-P. Gehrken, R. Swali, G. Skoropowski, P. J. Scheuer, J. Org. Chem. 1998, 63, 3221-3286.
2. [1b] R. B. Kinnel, H.-P. Gehrken, P. J. Scheuer, J. Am. Chem. Soc. 1993, 115, 3376-3377.
3. S. Forenza, L. Minale, R. Riccio, E. Fattorusso, J. Chem. Soc., Chem. Commun. 1971, 1129-1130.
4. E. E. Garcia, L. E. Benjamin, R. I. Fryer, J. Chem. Soc., Chem. Commun. 1973, 78-79.
5. G. Cimino, S. De Stefano, L. Minale, G. Sodano, Comp. Biochem. Physiol. 1975, 50B, 279-285.
6. G. Cimino, S. De Rosa, S. De Stefano, L. Mazzarella, R. Puliti, G. Sodano, Tetrahedron Lett. 1982, 23, 767-768.
7. J. N. A. Hooper, P. R. Bergquist, Memoirs of the Queensland Museum, 1992, 32, 99-137.
8. J. Kobayashi, Y. Ohizumi, H. Nakamura, K. Hirata, K. Wakamatsu, T. Miyazawa, Experientia, 1986, 42, 1064-1065.
9. P. A. Keifer, R. E. Schwartz, M. E. S. Koker, R. G. Hughes, Jr., D. Rittschof, K. L. Rinehart, J. Org. Chem. 1991, 56, 2965-2975.
10. R. Rosa, W. Silva, G. Escalona de Motta, A. D. Rodriguez, J. J. Morales, M. Ortiz, Experientia 1992, 48, 885-887.
11. R. B. Kinnel, H.-P. Gehrken, P. J. Scheuer, J. Am. Chem. Soc. 1993, 115, 3376-3377.
12. F. Cafieri, E. Fattorusso, A. Mangoni, O. Tagliatela-Scafati, R. Carnuccio, Bioorg. Med. Chem. Lett. 1995, 5, 799-804.
13. S. Tsukamoto, H. Kato, H. Hirota, N. Fusetani, J. Nat. Prod. 1996, 59, 501-503.
14. [13a] D. H. Williams, D. J. Faulkner, Tetrahedron 1996, 52, 5381-5390.
15. [13b] D. J. Faulkner, Nat. Prod. Rep. 2000, 17, 7-55.
16. [13c] D. J. Faulkner, Nat. Prod. Rep. 1998, 15, 113-158 and earlier reviews in this series.
17. [14a] J. E. Baldwin, R. C. Whitehead, Tetrahedron Lett. 1992, 2059-2062.
18. [14b] K. Jakubowicz, K. B. Abdeljelil, M. Herdemann, M.-T. Martin, A. Gatreau-Olesker, A. Al Mourabit, Christian Marazano, Bhupesh C. Das. J. Org. Chem. 1999, 64, 7381-7387.
19. L. H. Foley, G. Büchi, J. Am. Chem. Soc. 1982, 104, 1776-1777.
20. S. A. Fedoreyev, S. G. Iliyin, N. K. Utkina, O. B. Maxinov, M. V. Reshetnyak, Tetrahedron 1989, 45, 3487-3492.
21. M. D'Ambrosio, A. Guerriero, C. Debitus, J. Pusset, S. Leroy, F. Pietra, J. Chem. Soc., Chem. Comm 1993, 1305-1306.
22. S. Tsukamoto, H. Kato, H. Hirota, N. Fusetani, J. Nat. Prod. 1996, 59, 501-503.
23. S. Marchais, A. Al Mourabit. A. Ahond, C. Poupat, P. Potier, Tetrahedron Lett. 1999, 40, 5519-5522.
24. I. Kitagawa, M. Kobayashi, K. Kitanaka, M. Kido, Y. Kyogoku, Chem. Pharm. Bull. 1983, 31, 2321-2328.
25. J.-C. Braekman, D. Daloze, C. Stoller, R. W. M. Van Soest, Bioch. Syst. Ecol. 1992, 20, 417-431.
26. P. Andrade, R. Willoughby, S. A. Pomponi, R. G. Kerr, Tetrahedron Lett. 1999, 40, 4775-4778.
27. [23a] G. De Nanteuil, A. Ahond, J. Guilhem, C. Poupat, E. Tran Huu Dau, P. Potier, M. Pusset, J. Pusset, P. Laboute, Tetrahedron 1985, 41, 6019-6033.
28. [23b] G. De Nanteuil, A. Ahond, C. Poupat, O. Thoison, P. Potier, Bull. Soc. Chim. Fr. 1986, 813-816.
29. [23c] A. Ahond, M. Bedoya-Zurita, M. Colin, C. Fizames, P. Laboute, F. Lavelle, D. Laurent, C. Poupat, J. Pusset, M. Pusset, O. Thoison, P. Potier, C. R. Acad. Sci. Paris, série II, 1988, 307, 145-148.
30. [23d] A. Ahond, M. Bedoya-Zurita, M. Colin, C. Fizames, P. Laboute, F. Lavelle, D. Laurent, C. Poupat, J. Pusset, M. Pusset, O. Thoison, P. Potier, C. R. Acad. Sci. Paris, série II 1988, 307, 145-148.
31. [23e] A. Ahond, A. Al Mourabit, M. Bedoya-Zurita, R. Heng, R. Marquez-Braga, C. Poupat, P. Potier Tetrahedron 1992, 48, 4327-4346.
32. [23f] S. Daninos, A. Al Mourabit, A. Ahond, M. Bedoya-Zurita, C. Poupat, P. Potier, Bull. Soc. Chim. Fr. 1994, 131, 590-599.
33. [23g] A. Al Mourabit, M. Pusset, M. Chtourou, C. Gaigne, A. Ahond, C. Poupat P. Potier, J. Nat Prod. 1997, 60, 290-291.
34. [23h] S. Daninos-Zeghal, A. Al Mourabit, A. Ahond, C. Poupat, P. Potier, Tetrahedron 1997, 53, 7605-7614.
35. [23i] S. Marchais A. Al Mourabit, C. Poupat, A. Ahond, P. Potier Tetrahedron Lett. 1998, 39, 8085-8088.