A Ramberg-Backlund approach to exo-glycals

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8179-8182

  Griffin, Frank K ^a   Murphy, Paul V ^b   Paterson, Duncan E ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; FUCOSE; GALACTOSE; GLUCOSE; GLYCOSIDE; MANNOSE; OXIDE; RIBOSE; XYLOSE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032578741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01822-X     Document Type: Article

References (33)

1. 1. Wilcox, C. S.; Long, G. W.; Suh, H. Tetrahedron Lett. 1984, 25, 395-398.
2. 1H-NMR and NOE studies establish that 4b produced by RajanBabu et al. also has the Z-configuration).
3. 3. Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Caneva, E. J. Org. Chem. 1992, 57, 1304-1306; for a recent example see Rubinstenn, G.; Mallet, J.-M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
4. 3. Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Caneva, E. J. Org. Chem. 1992, 57, 1304-1306; for a recent example see Rubinstenn, G.; Mallet, J.-M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
5. 4. Johnson, C. R.; Johns, B. A. Synlett 1997, 1406-1408.
6. 5. (a) Nicotra, F.; Panza, L.; Russo, G. Tetrahedron Lett. 1991, 32, 4035-4038; see also Gervay, J.; Flaherty, T. M.; Hohnes, D. Tetrahedron 1997, 53, 16355-16364.
7. 5. (a) Nicotra, F.; Panza, L.; Russo, G. Tetrahedron Lett. 1991, 32, 4035-4038; see also Gervay, J.; Flaherty, T. M.; Hohnes, D. Tetrahedron 1997, 53, 16355-16364.
8. (b) Faivre-Buet, V.; Eynard, I.; Nga, H. N.; Descotes, G.; Grouiller, A. J. Carbohydr. Res. 1993, 12, 349-356.
9. 6. Brockhaus, M.; Lehmann, J. Carbohydr. Res. 1977, 53, 21-31; Lehmann, J.; Schwesinger, B. Carbohydr, Res. 1982, 107, 43-53 and references therein.
10. 6. Brockhaus, M.; Lehmann, J. Carbohydr. Res. 1977, 53, 21-31; Lehmann, J.; Schwesinger, B. Carbohydr, Res. 1982, 107, 43-53 and references therein.
11. 7. Csuk, R.; Glänzer, B. I. Tetrahedron 1991, 47, 1655-1664; Ali, M. H.; Collins, P. M.; Overend, W. G. Carbohydr. Res. 1990, 205, 428-434 and references therein.
12. 7. Csuk, R.; Glänzer, B. I. Tetrahedron 1991, 47, 1655-1664; Ali, M. H.; Collins, P. M.; Overend, W. G. Carbohydr. Res. 1990, 205, 428-434 and references therein.
13. 8. Fritz, H.; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 71-92; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 93-99; Brewer, C. F.; Hehre, E. J.; Lehmann, J.; Weiser, W. Liebigs Ann. 1984, 1078-1087; Vasella, A.; Witzig, C.; Waldraff, C.; Uhlmann, P.; Briner, K.; Bernet, B.; Panza, L.; Husi, R. Helv. Chim. Acta 1993, 76, 2847-2875.
14. 8. Fritz, H.; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 71-92; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 93-99; Brewer, C. F.; Hehre, E. J.; Lehmann, J.; Weiser, W. Liebigs Ann. 1984, 1078-1087; Vasella, A.; Witzig, C.; Waldraff, C.; Uhlmann, P.; Briner, K.; Bernet, B.; Panza, L.; Husi, R. Helv. Chim. Acta 1993, 76, 2847-2875.
15. 8. Fritz, H.; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 71-92; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 93-99; Brewer, C. F.; Hehre, E. J.; Lehmann, J.; Weiser, W. Liebigs Ann. 1984, 1078-1087; Vasella, A.; Witzig, C.; Waldraff, C.; Uhlmann, P.; Briner, K.; Bernet, B.; Panza, L.; Husi, R. Helv. Chim. Acta 1993, 76, 2847-2875.
16. 8. Fritz, H.; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 71-92; Lehmann, J.; Schlesselmann, P. Carbohydr. Res. 1983, 113, 93-99; Brewer, C. F.; Hehre, E. J.; Lehmann, J.; Weiser, W. Liebigs Ann. 1984, 1078-1087; Vasella, A.; Witzig, C.; Waldraff, C.; Uhlmann, P.; Briner, K.; Bernet, B.; Panza, L.; Husi, R. Helv. Chim. Acta 1993, 76, 2847-2875.
17. 9. Lakhrissi, M.; Chapleur, Y. J. Org. Chem. 1994, 59, 5752-5757 and references therein.
18. 10. Motherwell, W. B.; Tozer, M. J.; Ross, B. C. Chem. Commun. 1989, 1437-1439.
19. 11. (a) Mlynarski, J.; Banaszek, A. Tetrahedron Lett. 1998, 39, 5425-5428;
20. (b) Petasis, N. A.; Staszewski, J. P.; Fu, D.-K. Tetrahedron Lett. 1995, 36, 3619-3622.
21. 12. Lakhrissi, M.; Chapleur, Y. Angew. Chem. Int. Ed. Engl. 1996, 35, 750-752.
22. 13. Meyers, C. Y.; Malte, A. M.; Matthews, W. S. J. Am. Chem. Soc. 1969, 91, 7510-7512.
23. 14. Chan, T.-L.; Fong, S.; Li, Y.; Man, T.-O.; Poon, C. D. Chem. Commun. 1994, 1771-1772.
24. 15. Ramberg, L. ; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A, 1-50 ( Chem. Abstr. 1940, 34, 4725); for a recent review see Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991.
25. 15. Ramberg, L. ; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A, 1-50 ( Chem. Abstr. 1940, 34, 4725); for a recent review see Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991.
26. 15. Ramberg, L. ; Bäcklund, B. Ark. Kemi. Mineral. Geol. 1940, 27, Band 13A, 1-50 ( Chem. Abstr. 1940, 34, 4725); for a recent review see Clough, J. M. Ch. 3.8 in Comprehensive Organic Synthesis, Vol. 3, Eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991.
27. 16. a. Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydrate Res. 1995, 275, 179-184;
28. b. Holick, S. A.; Chiu, S.-H. L.; Anderson, L. Carbohydrate Res. 1976, 50, 215-225;
29. c. Susaki, H. Chem. Pharm. Bull. 1994, 42, 1917-1918.
30. 17. All new compounds were fully characterised by high field NMR spectroscopy and by elemental analysis and/or HRMS.
31. 18. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem. Int. Ed. Engl. 1995, 34, 909-912 and references therein.
32. 19. Boxwell, C.; Turkenburg, J. Unpublished results.
33. 20. Alcaraz, M.-L.; Griffin, F. K.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8183-8186.