Carbocycles from carbohydrates via free radical cyclizations: Synthesis and manipulation of annulated furanoses

Synlett

Volumn , Issue 7, 1998, Pages 693-699

  Marco Contelles, José ^a   Alhambra, Carolina ^a   Martínez Grau, Angeles ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001804167     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1754     Document Type: Article

References (46)

1. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983.
2. Hanessian, S. Preparative Carbohydrate Chemistry; Marcel Dekker: New York, 1997.
3. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986;
4. (b) Curran, D. P. Synthesis 1988, 417, 489;
5. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. A., Ed.; Pergamon: New York, 1991; vol 4; p 715, 779;
6. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237;
7. (e) RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139;
8. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
9. Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
10. (a) Fraser-Reid, B.; Anderson, R. C. Prog. Chem. Org. Nat. Prod. 1980, 39, 1;
11. (b) Fraser-Reid, B.; Tsang, R. In Strategies and Tactics in Organic Synthesis; Academic Press: New York, 1989; vol 2, p 123.
12. (a) King-Mo, S.; Giuliano, R. M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4774;
13. (b) Suryawanshi, S. N.; Dhami, T. S.; Bhakuni, D. S. Tetrahedron Lett. 1991, 32, 1519.
14. Prashad, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 1564.
15. Georges, M.; Tam, T.-F.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5747.
16. Gable, K. P.; Benz, G. A. Tetrahedron Lett. 1991, 32, 3473.
17. Hashimoto, H.; Furuichi, K.; Miwa, T. J. Chem. Soc. Chem. Commun. 1987, 1002.
18. Dickson, J. K. Jr.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1990, 1440.
19. Araki, Y.; Endo, T.; Arai, Y.; Tanji, M.; Ishido, Y. Tetrahedron Lett. 1989, 50, 2829.
20. (a) Audin, C.; Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1988, 29, 3691;
21. (b) De Mesmaeker, A.; Hoffmann, P.; Ernst, B. Tetrahedron Lett. 1989, 30, 57.
22. (a) Majumdar, S.; Bhattacharjya, A.; Patra, A. Tetrahedron Lett. 1997, 38, 8581;
23. (b) Czernecki, S.; Ayadi, E.; Xie, J. Tetrahedron Lett. 1996, 37, 9193;
24. (c) Xi, Z.; Glemarec, C.; Chattopadhyaya, J. Tetrahedron 1993, 49, 7525.
25. Tadano, K.-I.; Miyazaki, M.; Ogawa, S.; Suami, T. J. Org. Chem. 1988, 55, 1574.
26. Curran, D. P. Synlett 1991, 63.
27. Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160.
28. Giese, B.; González-Gómez, J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69.
29. McGuirk, P. R.; Collum, D. B. J. Am. Chem. Soc. 1982, 104, 4496.
30. Hanessian, S.; Dhanoa, D. S.; Beaulieu, P. Can. J. Chem. 1987, 65, 1859.
31. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925;
32. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH, 1995.
33. Marco-Contelles, J. Synth. Commun. 1994, 24, 1293.
34. (a) Marco-Contelles, J.; Martínez-Grau, A.; Bernabé, M.; Martin, N.; Seoane, C. Synlett 1991, 165;
35. (b) Marco-Contelles, J.; Martínez-Grau, A. Tetrahedron 1991, 47, 7663;
36. (c) Marco-Contelles, J.; Martínez-Grau, A.; Martínez-Ripoll, M.; Cano, H.; Foces-Foces, C. J. Org. Chem. 1992, 57, 403.
37. For the first report of a free radical cyclization onto an oxime ether in a sugar template, see: Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 110, 1633.
38. Reflecting the importance of this paper, some years later, we have largely developed the synthetic possibilities of oxime ethers in free radical cyclizations: Marco-Contelles, J.; Gallego, P.; Rodríguez-Fernández, M.; Khiar, N.; Destabel, C.; Bernabé, M.; Martínez-Grau, A.; Chiara, J. L. J. Org. Chem. 1997, 62, 7397 and references cited therein.
39. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377.
40. (a) Marco-Contelles, J.; Ruiz, P.; Sánchez, B.; Jimeno, M. L. Tetrahedron Lett. 1992, 33, 5261;
41. (b) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669.
42. For another approach, see: Rondot, B.; Durand, T.; Vidal, J.-R; Girard, J.-P.; Rossi, J.-C. J. Chem. Soc., Perkin Trans. 2 1995, 1589.
43. Marco-Contelles, J.; Ruiz, P.; Sánchez, B. J. Org. Chem. 1993, 58, 2894.
44. See also: Boivin, J.; Camara, J.; Zard, S. Z. J. Am. Chem. Soc. 1992, 114, 7909 and references cited therein.
45. RajanBabu, T. V.; Fukunaga, T.; Reddy, G. S. J. Am. Chem. Soc. 1989, 111, 1759.
46. Karabatsos, G. J.; Fenglio, D. J. Top. Stereochem. 1970, 5, 167.