A new approach to erythrinanes through Pummerer-type cyclization

European Journal of Organic Chemistry

Volumn , Issue 4, 1999, Pages 909-915

  Jousse, Céline ^a   Desmaële, Didier ^a  

^a CNRS   (France)

Author keywords

Erythrina alkaloids; Michael addition; Nitro aldol reaction; Nitrogen heterocycles; Pummerer reaction

Indexed keywords

ERYTHRINA ALKALOID; ERYTHRINANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DESULFURIZATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0345425796     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199904)1999:4<909::aid-ejoc909>3.0.co;2-7     Document Type: Article

References (54)

1. For recent reviews, see: [1a] S. F. Dyke, S. N. Quessy in The Alkaloids (Ed.: R. G. A. Rodrigo), Academic Press, New York, 1981, vol. 18, p. 1-98.
2. [1b] A. S. Chawla, V. K. Kapoor in Alkaloids: Chemical and Biological Perspectives (Ed.: S. W. Pelletier), Pergamon, 1995, vol. 9, p. 86-153.
3. [2a] S. Ghosal, S. K. Dutta, S. K. Bhattacharya, J. Pharm. Sci. 1972, 61, 1274-1277.
4. [2b] M. Williams, J. L. Robinson, J. Neuroscience 1984, 4, 2906-2911.
5. [2c] M. W. Decker, M. J. Anderson, J. D. Brioni, D L. Donnelly-Roberts, C. H. Kang, A. B. O'Neill, M. Piattoni-Kaplan, S. Swanson, J. P. Sullivan, Eur. J. Pharmacol. 1995, 280, 79-89.
6. B. Belleau, J. Am. Chem. Soc. 1953, 75, 5765-5766.
7. [4a] A. Mondon, Angew. Chem. 1956, 68, 578.
8. [4b] A. Mondon, G. Hasselmeyer, J. Zander, Chem. Ber. 1959, 92, 2543-2552.
9. [4c] A. Mondon, K. F. Hansen, Tetrahedron Lett. 1960, 5-8.
10. For recent related strategies, see: [5a] H. Ishibashi, K. Sato, M. Ikeda, M. Maeda, S. Akai, Y. Tamura, J. Chem. Soc., Perkin Trans. 1 1985, 605-606.
11. [5b] J. H. Rigby, M. Qabar, J. Am. Chem. Soc. 1991, 113, 8975-8976.
12. [5c] A. Padwa, R. Hennig, C. O. Kappe, T. S. Reger, J. Org. Chem. 1998, 63, 1144-1155.
13. [6a] V. Prelog, Angew. Chem. 1957, 69, 33-39.
14. [6b] R. V. Stevens, M. Wentland, J. Chem. Soc., Chem. Commun. 1968, 1104-1105.
15. [7a] T. Sano, J. Toda, N. Kashiwaba, Y. Tsuda, Y. Iitaka, Heterocycles 1981, 16, 1151-1156.
16. [7b] T. Sano, J. Toda, Y. Horiguchi, K. Imafuku, Y. Tsuda, Heterocycles 1981, 16, 1463-1468.
17. [7c] T. Sano, J. Toda, Y. Tsuda, T. Ohshimu, Heterocycles 1984, 22, 49-52.
18. H. H. Wasserman, R. M. Amici, J. Org. Chem. 1989, 54, 5843-5844.
19. C.-T. Chou, J. S. Swenton, J. Am. Chem. Soc. 1987, 109, 6898-6899.
20. [10a] H. Irie, K. Shibata, K. Matsuno, Y. Zhang, Heterocycles 1989, 29, 1033-1035.
21. [10b] S. J. Danishefsky, J. S. Panek, J. Am. Chem. Soc. 1987, 109, 917-918.
22. [10c] R. Ahmed-Schofield, P. S. Mariano, J. Org. Chem. 1987, 52, 1478-1482.
23. [11a] J. E. Gervay, F. McCapra, T. Money, G. M. Sharma, A. I. Scott, J. Chem. Soc., Chem. Commun. 1966, 142-143.
24. [11b] A. Mondon, M. Ehrhardt, Tetrahedron Lett. 1966, 2557-2568.
25. [11c] H. Tanaka, M. Shibata, K. Ito, Chem. Pharm. Bull. 1984, 32, 1578-1582.
26. [12a] M.-A. Le Dréau, D. Desmaële, F. Dumas, J. d'Angelo, J. Org. Chem. 1993, 58, 2933-2935.
27. [12b] D. Desmaële, J. M. Louvet, Tetrahedron Lett. 1994, 35, 2549-2552.
28. [12c] C. Jousse, D. Mainguy, D. Desmaële, Tetrahedron Lett. 1998, 38, 1349-1352.
29. N. Kornblum, W. M. Weaver, J. Am. Chem. Soc. 1958, 80, 4333-4337.
30. [14a] L. Weisler, R. W. Helmkamp, J. Am. Chem. Soc. 1945, 67, 1167-1171.
31. [14b] A. R. Katritzky, G. De Ville, R. C. Patel, Tetrahedron 1981, 37, Suppl. 1, 25-30.
32. J. M. Takacs, M. A. Helle, F. L. Seely, Tetrahedron Lett, 1986, 27, 1257-1260.
33. C. Botteghi, F. Soccolini, Synthesis 1985, 592-604.
34. F. M. Hauser, V. M. Baghdanov, J. Org. Chem. 1988, 53, 4676-4681.
35. G. Rosini, R. Ballini, M. Petrini, Synthesis 1983, 1014-1016.
36. G. Rosini, R. Ballini, M. Petrini, P. Sorrenti, Tetrahedron 1984, 40, 3809-3814.
37. P. Knochel, D. Seebach, Synthesis 1982, 1017-1018.
38. E. M. Burgess, H. R. Penton Jr., E. A. Taylor, J. Org. Chem. 1973, 38, 26-31.
39. R. O. Hutchins, D. Rotstein, N. Natale, J. Fanelli, D. Dimmel, J. Org. Chem. 1976, 41, 3328-3329.
40. D. A. White, M. M. Baizer, Tetrahedron Lett. 1973, 3597-3600.
41. P. Bakó, A. Szöllõsy, P. Bombicz, L. Tòke, Synlett 1997, 291-292.
42. R. Ballini, P. Marziali, A. Mozzicafreddo, J. Org. Chem. 1996, 67, 3209-3211.
43. [26a] N. Ono, A. Kamimura, A. Kaji, Synthesis 1984, 226-227.
44. [26b] R. Ballini, G. Bosica, Tetrahedron 1995, 51, 4213-4222.
45. Formation of ketone 26 before any acidic work-up precludes a Nef-type mechanism.
46. Y. Nakashita, M. Hesse, Helv. Chim. Acta 1983, 66, 845-860.
47. C. D. Weis, G. R. Newkome, Synthesis 1995, 1053-1065.
48. J. B. Hendrickson, R. W. Alder, D. R. Dalton, D. G. Hey, J. Org. Chem. 1969, 34, 2667-2676.
49. PCMODEL (88.1), Serena Software, Box 3076, Bloomington, IN 47402-3076, USA, 1987.
50. [32a] P. perlmutter in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, New York, Seoul, Tokyo, 1992, chapter 6, p. 310-321.
51. [32b] Intramolecular conjugate addition of carbamate anions to vinyl sulfoxides has been reported: M. Hirama, H. Hioki, S. Itô, C. Kabuto, Tetrahedron Lett. 1988, 29, 3121-3124.
52. O. De Lucchi, U. Miotti, G. Modena, Org. React. 1991, 40, 157-405.
53. E. Dagne, W. Steglich, Phytochemistry 1984, 23, 449-451.
54. A. Mondon, P.-R. Seidel Chem. Ber. 1971, 104, 2937-2959.