A new synthetic approach to dioxoaporphines - Application to the synthesis of N-methylouregidione

European Journal of Organic Chemistry

Volumn , Issue 13, 2001, Pages 2559-2567

  Hoarau, Christophe ^a   Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

Cyclizations; Enamines; Horner reaction; Nitrogen heterocycles; Photolysis

Indexed keywords

APORPHINE DERIVATIVE; HETEROCYCLIC COMPOUND; N METHYLOUREGIDIONE; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ORGANIC CHEMISTRY; PHOTOLYSIS; SYNTHESIS;

EID: 0034959081     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200107)2001:13<2559::AID-EJOC2559>3.0.CO;2-3     Document Type: Article

References (58)

1. [1a] I. N. Southon, J. Buckingham, Dictionary of Alkaloids, Chapman and Hall, London, 1989.
2. [1b] T. Kametani, Aporphine Alkaloids in The Alkaloids (Ed.: A. Brossi), Academic Press Inc., New York, 1982, vol. XXIV, chapter 4, pp. 153-251.
3. [1c] H. Guinaudeau, M. Leboeuf, A. Cave, Lloydia 1975, 38, 275-338.
4. [1d] H. Guinaudeau, M. Leboeuf, A. Cave, J. Nat. Prod. 1979, 42, 325-360.
5. [1e] H. Guinaudeau, M. Leboeuf, A. Cave, J. Nat. Prod. 1983, 46, 761-835
6. [1f] H. Guinaudeau, M. Leboeuf, A. Cave, J. Nat. Prod. 1988, 51, 389-474.
7. [1g] H. Guinaudeau, M. Leboeuf, A. Cave, J. Nat. Prod. 1994, 57, 1033-1135.
8. L. Castedo, A. Mouriño, R. Suau, Tetrahedron Lett. 1976, 501-502.
9. E. M. K. Wijeratne, A. A. L. Gunatilaka, D. G. I. Kingston, R. C. Haltiwanger, D. S. Eggleston, Tetrahedron 1995, 51, 7877-7882.
10. C.-L. Chen, H.-M. Chang, E. B. Cowling, Phytochemistry 1976, 15, 1161-1167.
11. [5a] V. S. Parmar, M. E. Bracke, J. Philippe, J. Wengel, S. C. Jain, C. E. Olsen, K. S. Bisht, N. K. Sharma, A. Courtens, S. K. Sharma, K. Vennekens, V. V. Marck, S. K. Singh, N. Kumar, A. Kumar, S. Malhotra, R. Kumar, V. K. Rajwanshi, R. Jain, M. M. Mareel, Bioorg. Med. Chem. 1997, 36, 1609-1619.
12. [5b] J. D. Park, N. I. Baek, Y. H. Lee, S. I. Kim, Arch. Pharm. Res. 1996, 19, 559-561.
13. [5c] T. H. Broschard, M. Wiessler, H. H. Schmeiser, Cancer Lett. 1995, 98, 47-56.
14. [5d] T.-S. Wu, L.-F. Ou, C.-M. Teng, Phytochemistry. 1994, 36, 1063-1068.
15. [5e] T. H. Broschard, M. Wiessler, C.-W. von der Lieth, H. H. Schmeiser, Carcinogenesis 1994, 15, 2331-2340.
16. [5f] J. Hinou, C. Demetzos, C. Harvala, C. Rossakis, Int. J. Crude Drug Res. 1990, 28, 149-151.
17. [5g] S. Chakraborty, R. Nandi, M. Maiti, B. Achari, C. R. Saha, S. C. Pakrashi, Biochem. Pharmacol. 1989, 38, 3683-3687.
18. [5h] J. M. Pezzuto, S. M. Swanson, W. Mar, C.-T. Che, G. A. Cordell, H. H. S. Fong, Mutation Research 1988, 206, 447-454.
19. [5i] N.-J. Sun, M. Antoun, C.-J. Chang, J. M. Cassidy, J. Nat. Prod. 1987, 50, 843-846.
20. L. Castedo, J. Fumega, R. Riguera, J. M. Saá, R. Suau, An. Quim. 1978, 74, 164-165.
21. [7a] J.-I. Kunitomo, Y. Murakami, M. Oshikata, T. Shingu, M. Akasu, S.-T. Lu, I.-S. Chen, Phytochemistry 1980, 19, 2735-2740.
22. [7b] J. M. Saá, M. J. Mitchell, M. P. Cava, Tetrahedron Lett. 1976, 601-602.
23. [8a] L. Castedo, R. Estévez, J. M. Saá, R. Suau, Tetrahedron Lett. 1978, 2179-2182.
24. [8b] L. Castedo, R. J. Estévez, J. M. Saá, R. Suau, J. Heterocycl. Chem. 1982, 19, 1319-1323.
25. [9a] J. C. Estévez, C. M. Villaverde, R. J. Estévez, L. Castedo, Tetrahedron 1994, 50, 2107-2114.
26. [9b] J. C. Estévez, C. M. Villaverde, R. J. Estévez, L. Castedo, Heterocycles 1994, 38, 1-4.
27. [10a] L. Castedo, E. Guitián, J. M. Saá, R. Suau, Tetrahedron Lett. 1982, 23, 457-458.
28. [10b] N. Atanes, L. Castedo, E. Guitián, C. Saá, J. M. Saá, R. Suau, J. Org. Chem. 1991, 56, 2984-2988.
29. R. Suau, J. M. López-Romero, R. Rico, F. J. Alonso, C. Lobo, Tetrahedron 1996, 52, 11307-11320.
30. [12a] R. Suau, J. M. López-Romero, R. Rico, Tetrahedron 1997, 53, 14397-14410.
31. [12b] R. Suau, J. M. López-Romero, R. Rico, Tetrahedron Lett. 1996, 37, 9357-9360.
32. J.-m. Fu, B.-p. Zhao, M. J. Sharp, V. Snieckus, J. Org. Chem. 1991, 56, 1683-1685.
33. L. Benesch, P. Bury, D. Guillaneux, S. Houldsworth, X. Wang, V. Snieckus, Tetrahedron Lett. 1998, 39, 961-964.
34. A. Couture, E. Deniau, P. Grandclaudon, P. Woisel, Tetrahedron 1996, 52, 4433-4448.
35. [16a] S. Takanashi, K. Mori, Eur. J. Org. Chem. 1998, 43-45.
36. [16b] W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408.
37. [16c] H. J. Hensel, P. L. Fuchs, Synth. Commun. 1986, 16, 1285-1295.
38. [17a] A Couture, E. Deniau, P. Grandclaudon, C. Hoarau, J. Org. Chem. 1998, 63, 3128-3132.
39. [17b] A. Couture, E. Deniau, P. Grandclaudon, Synlett 1997, 1475-1478.
40. [17c] A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau, Tetrahedron 2000, 56, 1491-1499.
41. [18a] A Couture, E. Deniau, P. Woisel, P. Grandclaudon, Synthesis 1997, 1439-1445.
42. [18b] C. Hoarau, A. Couture, E. Deniau, P. Grandclaudon, Synthesis 2000, 655-660.
43. J. Rohovec, P. Vojtisek, I. Lukes, Phosphorus Sulfur Silicon Relat. Elem. 1999, 148, 79-95.
44. S. F. Martin, J. Org. Chem. 1976, 41, 3337-3338.
45. N. L. J. M. Broekhof, P. van Elburg, A. van der Gen, Recl. Trav. Chim. Pays-Bas 1984, 103, 312-316;
46. Chem. Abstr. 1985, 102, 113606.
47. N. L. J. M. Broekhof, P. van Elburg, D. J. Hoff, A. van der Gen, Recl. Trav. Chim. Pays-Bas 1984, 103, 317-321;
48. Chem. Abstr. 1985, 102, 94908.
49. [23a] U. E. Matter, C. Pascual, E. Pretsch, A. Pross, W. Simon, S. Sternhell, Tetrahedron 1969, 25, 691-697.
50. [23b] F. Babudri, V. Fiandanese, R. Musio, F. Naso, O. Sciavovelli, A. Scilimati, Synthesis 1991, 225-228.
51. B. K. Banik, Curr. Org. Chem. 1999, 3, 469-496.
52. Y. Lear, T. Durst, Can. J. Chem. 1997, 75, 817-824.
53. D. C. Harrowven, N. A. Newman, C. A. Knight, Tetrahedron Lett. 1998, 39, 6757-6760.
54. E. Wright, J. Org. Chem. 1946, 11, 111-117.
55. J. M. Domagala, T. H. Haskell, J. Org. Chem. 1981, 46, 134-140.
56. E. McDonald, P. Smith, J. Chem. Soc., Perkin Trans. 1 1980, 837-842.
57. R. Bartnik, G. Mloston, Tetrahedron 1984, 40, 2569-2576.
58. K. Mahmood, K. C. Chan, M. H. Park, Y. N. Han, B. H. Han, Phytochemistry 1986, 25, 1509-1510.