Prodigiosin synthesis with electron rich 2,2′-bipyrroles

Canadian Journal of Chemistry

Volumn 86, Issue 3, 2008, Pages 213-218

  Jolicoeur, Benoit ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Bipyrrole; PNU 156804; Prodigiosin; Pyrrole; Undecylprodigiosin

Indexed keywords

CONDENSATION; ELECTRONS; METABOLITES; OLEFINS; OXIDATION;

BIPYRROLES; IMMUNOMODULATING PROPERTIES;

SYNTHESIS (CHEMICAL);

EID: 41549115898     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V07-150     Document Type: Article

References (44)

1. J.W. Bennett and R. Bentley. Adv. Appl. Microbiol. 47, 1 (2000).
2. A. Fürstner. Angew. Chem. Int. Ed. 42, 3582 (2003).
3. R.A. Manderville. Curr. Med. Chem.- Anti-Cancer Agents, 1, 195 (2001).
4. B. Montaner and R. Pérez-Tomás. Curr. Cancer Drug Targets, 3, 57 (2003).
5. C.M. Baldino, J. Parr, C.J. Wilson, S.C. Ng, D. Yohannes, and H.H. Wasserman. Bioorg. Med. Chem. Lett. 16, 701, (2006).
6. D.M. Pinkerton, M.G. Banwell, and A.C. Willis. Org. Lett. 9, 5127 (2007).
7. J.T. Reeves. Org. Lett. 9, 1879 (2007).
8. S.G. Salamone and G.B. Dudley. Org. Lett. 7, 4443 (2005).
9. J.Q.H. La, A.A. Michaelides, and R.A. Manderville. J. Phys. Chem. B, 111, 11803 (2007).
10. D.L. Boger and M. Patel. J. Org. Chem. 53, 1405 (1988).
11. M. Isaka, A. Jaturapat, J. Kramyu, M. Tanticharoen, and Y Thebtaranonth. Antimicrob. Agents Chemother. 46, 1112 (2002).
12. H.S. Kim, M. Hayashi, Y. Shibata, Y. Wataya, T. Mitamura, T. Horii, K. Kawauchi, H. Hirata, S. Tsuboi, and Y. Moriyama. Biol. Pharm. Bull. 22, 532 (1999).
13. J.E.H. Lazaro, J. Nitcheu, R.Z. Predicala, G.C. Mangalindan, F. Nesslany, D. Marzin, G.P. Concepcion, and B. Diquet. J. Nat. Toxins, 11, 367 (2002).
14. S. Songia, A. Mortellaro, S. Taverna, C. Fomasiero, E.A. Scheiber, E. Erba, F. Colotta, A. Mantovani, A.M. Isetta, and J. Golay. J. Immunol. 158, 3987 (1997).
15. R. D'Alessio, A. Bargiotti, O. Carlini, F. Colotta, M. Ferrari, P. Gnocchi, A. Isetta, N. Mongelli, P. Motta, A. Rossi, M. Rossi, M. Tibolla, and E. Vanotti. J. Med. Chem. 43, 2557 (2000).
16. A. Mortellaro, S. Songia, P. Gnocchi, M. Ferrari, C. Fornasiero, R. D'Alessio, A. Isetta, F. Colotta, and J. Golay. J. Immunol. 162, 7102 (1999).
17. V. Rizzo, A. Morelli, V. Pinciroli, D. Sciangula, and R. D'Alessio. J. Pharm. Sci. 88, 73 (1999).
18. S.M. Stepkowski, R.A. Erwin-Cohen, F. Behbod, M.E. Wang, X. Qu, N. Tejpal, Z.S. Nagy, B.D. Kahan, and R.A. Kirken, Blood, 99, 680 (2002).
19. B. Jolicoeur and W.D. Lubell. Org. Lett. 8, 6107 (2006).
20. W.R. Hearn, M.K. Elson, R.H. Williams, and J. Medina-Castro. J. Org. Chem. 35, 142 (1970).
21. H. Rapoport and K.G. Holden. J. Am. Chem. Soc. 84, 635 (1962).
22. For syntheses of aldehyde 4 see: K. Dairi, S. Tripathy, G. Attardo, and J.-F. Lavallée. Tetrahedron Lett. 47, 2605 (2006), and refs. cited therein.
23. R. D'Alessio and A. Rossi. Synlett, 6, 513 (1996).
24. D. Brown, D. Griffiths, M.E. Rider, and R.C. Smith. J. Chem. Soc. Perkin Trans. 1, 455 (1986).
25. T. Benincori, E. Brenna, F. Sannicolo, G. Zotti, S. Zecchin, G. Schiavon, C. Gatti, and G. Frigerio. Chem. Mater. 12, 1480 (2000).
26. C. Gatti, G. Frigerio, T. Benincori, E. Brenna, F. Sannicolo, G. Zotti, S. Zecchin, and G. Schiavon. Chem. Mater. 12, 1490 (2000).
27. G. Zotti, S. Zecchin, G. Schiavon, and A. Berlin. Chem. Mater. 14, 3607 (2002).
28. A. Merz, S. Anikin, B. Lieser, J. Heinze, and H. John. Chem. Eur. J. 9, 449 (2003).
29. J. Bordner and H. Rapoport. J. Org. Chem. 30, 3824 (1965).
30. A. Fürstner, J. Grabowski, and C.W. Lehmann. J. Org. Chem. 64, 8275 (1999).
31. M. Yu, D. Pantos, J.L. Sessler, and B.L. Pagenkopf. Org. Lett. 6, 1057 (2004).
32. A.A. Dörr and W.D. Lubell. Can. J. Chem. 85, 1006 (2007).
33. K.A. Hansford, J.E. Dettwiler, and W.D. Lubell. Org. Lett. 5, 4887 (2003).
34. K.A. Hansford, V. Zanzarova, A. Dorr, and W.D. Lubell. J. Comb. Chem. 6, 893 (2004).
35. A.J. Mancuso, S.L. Huang, and D. Swern. J. Org. Chem. 43, 2480 (1978).
36. B. Jolicoeur, E.E. Chapman, A. Thompson, and W.D. Lubell. Tetrahedron, 62, 11531 (2006).
37. W.S. Yu, Y. Mei, Y Kang, Z.M. Hua, and Z.D. Jin. Org. Lett. 6, 3217 (2004).
38. H.S. Broadbent, W.S. Burnham, R.K. Olsen, and R.M. Sheeley. J. Heterocycl. Chem. 5, 757 (1968).
39. W. Hinz, R.A. Jones, S.U. Patel, and M.H. Karatza, Tetrahedron, 42, 3753 (1986).
40. M.J. Hall, S.O. McDonnell, J. Killoran, and D.F. O'Shea. J. Org. Chem. 70, 5571 (2005).
41. F. Lucchesini. Tetrahedron, 48, 9951 (1992).
42. H.H. Wasserman and L.J. Lombardo. Tetrahedron Lett. 30, 1725 (1989).
43. H.H. Wasserman, A.K. Petersen, M.D. Xia, and J.J. Wang. Tetrahedron Lett. 40, 7587 (1999).
44. H.H. Wasserman, G.C. Rodgers, and D.D. Keith. Tetrahedron, 32, 1851 (1976).