Radical cyclization of O-glycosides using 1,1,2,2-tetraphenyldisilane as a radical reagent: Preparation of bicyclic sugars

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5440-5442

  Yamazaki, Osamu ^a   Yamaguchi, Kentaro ^a   Yokoyama, Masataka ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; RADICAL;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034714484     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0005971     Document Type: Article

References (29)

1. (a) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: Paris, 1995.
2. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
3. (c) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992.
4. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Organic Reactions; John Wiley & Sons: New York, 1996; Vol. 48, Chapter 2, "Radical Cyclization Reactions".
5. (a) Curran, D. P. Synthesis 1988, 417-439.
6. (b) Curran, D. P. Synthesis, 1988, 489-513.
7. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
8. (d) Neumann, W. P. Synthesis 1987, 665-683.
9. (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
10. (b) Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. The Chemistry of Organic Silicon Compounds; John Wiley & Sons: New York, 1998; Vol. 2, Chapter 25.
11. (a) Yamazaki, O.; Togo, H.; Matsubayashi, S.; Yokoyama, M. Tetrahedron Lett. 1998, 39, 1921-1924.
12. (b) Yamazaki, O.; Togo, H.; Matsubayashi, S.; Yokoyama, M. Tetrahedron 1999, 55, 3735-3747.
13. (c) Yamazaki, O.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 2891-2896.
14. (a) Jalali-Naini, M.; Lallemand, J. Y. Tetrahedron Lett. 1986, 27, 497-500.
15. (b) Ley, S. V.; Santafianos, D.; Blaney, W. M.; Simmonds, M. S. J. Tetrahedron Lett. 1987, 28, 221-224.
16. (c) Pflieger, D.; Muckensturm, B. Tetrahedron Lett. 1987, 28, 1519-1522.
17. (a) Audin, C.; Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1988, 29, 3691-3694.
18. (b) De Mesmaeker, A.; Hoffmann, P.; Ernst, B. Tetrahedron Lett. 1988, 29, 6585-6588.
19. (c) Chapleur, Y.; Moufid, N. J. Chem. Soc., Chem. Commun. 1989, 39-40.
20. (d) De Mesmaeker, A.; Hoffinann, P.; Ernst, B. Tetrahedron Lett. 1989, 30, 57-60.
21. (e) Ferrier, R. J.; Petersen, P. M.; Taylor, M. A. J. Chem. Soc., Chem. Commun. 1989, 1247-1248.
22. (f) De Mesmaeker, A.; Hoffmann, P.; Ernst, B.; Hug, P.; Winkler, T. Tetrahedron Lett. 1989, 30, 6307-6310.
23. (g) De Mesmaeker, A.; Hoffmann, P.; Ernst, B.; Hug, P.; Winkler, T. Tetrahedron Lett. 1989, 30, 6311-6314.
24. (h) Ferrier, R. J.; Petersen, P. M. Tetrahedron 1990, 46, 1-11.
25. (i) De Mesmaeker, A.; Hoffmann, P.; Winkler, T.; Waldner, A. Synlett 1990, 201-204.
26. (j) Moufid, N.; Chapleur, Y.; Mayon, P. J. Chem. Soc., Perkin Trans. 1 1992, 991-998.
27. (k) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369-5380.
28. (l) Mayer, S.; Prandi, J.; Bamhaoud, T.; Bakkas, S.; Guillou, O. Tetrahedron 1998, 54, 8753-8770.
29. -3. R factor = 0.082 for 1171 independent observed reflections (1 > 3.20σ(I)); weighted RW factor = 0.099.