Homoarcyriaflavin: Synthesis of ring-expanded arcyriaflavin analogues

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8130-8137

  Mahboobi, Siavosh ^a   Burgemeister, Thomas ^a   Dove, Stefan ^a   Kuhr, Sabine ^a   Popp, Alfred ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033615517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981926g     Document Type: Article

References (39)

1. Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844.
2. Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011-4014.
3. Pearce, C. J.; Doyle, T. W.; Forenza, S.; Lam, K. S.; Schroeder, D. R. J. Nat. Prod. 1988, 51, 937-940.
4. Pereira, E. R.; Belin, L.; Sancelme, M.; Prudhomme, M.; Ollier, M. J. Med. Chem. 1996, 39, 4471-4477.
5. Trinks, U.; Buchdunger, E.; Furet, P.; Kump, W.; Mett, H. J. Med. Chem. 1994, 37, 1015-1027.
6. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1894, 47, 792-798.
7. Davis, P. D.; Elliott, L. H.; Harris, W.; Hill, C. H.; Hurst, S. A.; Keech, E.; Kumar, M. K. H.; Lawton, G.; Nixon, J. S.; Wilkinson, S. E. J. Med. Chem. 1992, 35, 994-1001.
8. Toullec, D.; Pianetti, P.; Coste, H.; Bellevergue, P.; Grand-Perret, T.; Ajakane, M.; Baudet, V.; Boissin, P.; Boursier, E.; Loriolle, F.; Duhamel, L.; Charon, D.; Kirilovsky, J. J. Biol. Chem. 1991, 266, 15771-15781.
9. Davis, P. D.; Hill, C. H.; Lawron, G.; Nixon, J. S.; Wilkinson, S. E.; Hurst, S. A.; Keech, E.; Turner, S. E. J. Med. Chem. 1992, 35, 177-184.
10. Davis, P. D.; Hill, C. H.; Keech, E.; Lawton, G.; Nixon, J. S.; Sedgwick, A. D.; Wadsworth, J.; Westmacott, D.; Wilkinson, S. E. FEBS Lett. 1989, 259, 61-63.
11. Steglich, W.; Steffan, B.; Kopanski, L.; Eckhardt, G. Angew. Chem. 1980, 92, 463-464.
12. Hartenstein, J. H.; Aranda, J.; Barth, H.; Betche, H. J.; Kleinschroth, J.; Rudolph, C.; Reck, R.; Trostmann, U.; Schächtele, C. In Perspectives in Medicinal Chemistry; Testa, B., Fuhrer, W., Kyburz, E., Giger, R., Eds.; Verlag Helvetica Chimica Acta und VCH: Weinheim, New York, Basel, Cambridge, 1993; pp 99-118.
13. Gillig, J. R.; Jirousek, M. R. (Eli Lilly and Co.) US Patent Appl. 413,311, 1996; Chem. Abstr. 1996, 125, P 247615f.
14. Gillig, J. R.; Jirousek, M. R. (Eli Lilly and Co.) US Patent Appl. 413,311, 1996; Chem. Abstr. 1996, 125, P 247615f.
15. Heath, W. F.; Jirousek, M. R.; Mcdonald, J. H.; Rito, C. J. (Eli Lilly and Co.), Eur. Pat. Appl. 657, 458 A1, 1995; Chem. Abstr. 1996, 123, P 314033p.
16. Heath, W. F.; Jirousek, M. R.; Mcdonald, J. H.; Rito, C. J. (Eli Lilly and Co.), Eur. Pat. Appl. 657, 458 A1, 1995; Chem. Abstr. 1996, 123, P 314033p.
17. Heath, W. F.; Jirousek, M. R.; Mcdonald, J. H.; Rito, C. J.; Winneroski, L. L. (Eli Lilly and Company), Eur. Patent Appl. 657,411 A1, 1995; Chem. Abstr. 1996, 125, P 328740v.
18. Heath, W. F.; Jirousek, M. R.; Mcdonald, J. H.; Rito, C. J.; Winneroski, L. L. (Eli Lilly and Company), Eur. Patent Appl. 657,411 A1, 1995; Chem. Abstr. 1996, 125, P 328740v.
19. Heath, W. F.; McDonald, J. H.; Paal, M.; Rühter, G.; Schotten, T.; Stenzel, W. (Eli Lilly and Co.), US Patent Appl. 324,948, 1996;
20. Chem. Abstr. 1996, 123, P 339733d.
21. Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552-553.
22. Bergman, J.; Pelcman, B. J. Org. Chem. 1989, 54, 824-828.
23. Ohkubo, M.; Kawamoto, H.; Ohno, T.; Nakano, M.; Morishima, H. Tetrahedron 1997, 53, 585-592.
24. Moody, C. J.; Rahimtoola, K. F.; Porter, B.; Ross, B. C. J. Org. Chem. 1992, 57, 2105-2114.
25. Julia, M.; Manoury, P. Bull. Soc. Chim. France 1964, 1953-1956.
26. Kleinschroth, J.; Hartenstein, J.; Rudolph, C.; Schächtele, C. Bioorg. Med. Chem. Lett. 1995, 5, 55-60.
27. Gribble, G. W.; Berthel, S. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, London, New York, Tokyo, 1993; Vol. 12 (Part H), pp 365-409.
28. Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49, 4518-4523.
29. Leon, P.; Garbay-Jaureuiberry, C.; LePecq, J.-B.; Roques, B. P. Tetrahedron Lett. 1985, 27, 4923-4929.
30. Smith, A. B. I.; Visnick, M. Tetrahedron Lett. 1985, 26, 3757-3760.
31. Schmidt, E. K. G. Chem. Ber. 1974, 107, 2440-2452.
32. Scharf, H. D.; Korte, F.; Seidler, H.; Dittner, R. Chem. Ber. 1965, 98, 8, 764-780.
33. Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015-4018.
34. Gallant, M.; Link, J. T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 343-349.
35. Crystallographic data for the reported structure have been deposited at the Cambridge Crystallographic Data Centre, no. CCDC 116076.
36. Burnett, M. N.; Johnson, C. K. ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.
37. Günther, H. NMR-Spektroskopie; 3rd ed.; Georg Thieme Verlag: Stuttgart, New York, 1992.
38. Oki, M. In Methods in Stereochemical Analysis; Merchand, A. P., Ed.; VCH Publishers Inc.: Deerfield Beach, 1985; Vol. 4, pp 287-324.
39. Hickmott, R. W.; Wood, S.; Murray-Rust, P. J. Chem. Soc., Perkin Trans. 1 1985, 2033-2038.