Preparation of C-1 glycals via olefin metathesis. A convergent and flexible approach to C-glycoside synthesis

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1770-1771

  Calimente, Daniel ^a   Postema, Maarten H D ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; GLYCAL; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033583130     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982331o     Document Type: Article

References (48)

1. Dedicated to the memory of Professor Michael G. Hogben, Concordia University, Montreal.
2. (a) Evans, P. A.; Murthy, V. S. J. Org. Chem. 1998, 63, 6768-6769.
3. (b) Limanto, J.; Snapper, M. L. J. Org. Chem. 1998, 63, 6440-6441.
4. (c) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
5. (d) Renaud, J.; Quellet, S. G. J. Am. Chem. Soc. 1998, 120, 7995-7996.
6. (e) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298.
7. For recent reviews on olefin metathesis chemistry, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
8. (b) Ivin, K. J. J. Mol. Catal. A-Chem. 1998, 133, 1-16.
9. (c) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A-Chem. 1998, 133, 29-40.
10. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
11. (e) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
12. (f) Fürstner, A. Top. Catal. 1997, 4, 285-299.
13. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
14. (b) Feldman, J.; Murdzek, J. S.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 2260-2265.
15. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
16. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
17. (c) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
18. (d) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
19. For newly developed ruthenium-based metathesis catalysts, see: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1988, 37, 2490-2493.
20. (b) Wolf, J.; Stüer, W.; Grünwald, C.; Werner, H.; Schwab, P.; Schulz, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1124-1126.
21. For some recent examples of the application of the olefin metathesis reaction to carbohydrates, see: (a) Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998 39, 9623-9626.
22. (b) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043-4046.
23. (c) O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 7427-7430.
24. For reviews on C-glycoside synthesis, see: (a) Du, Y.; Lindhart, R. J. Tetrahedron 1998, 64, 9913-9959.
25. (b) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717.
26. (c) Postema, M. H. D.C-Glycoside Synthesis, 1st ed.; CRC Press: Boca Raton, 1995.
27. (d) Leyy, D. E.; Tang, C. The Chemistry of C-Glycosides, 1st ed.; Elsevier Science: Oxford, 1995; Vol. 13.
28. For some recent examples of C-glycoside synthesis see: (a) Wamhoff, H.; Warnecke, H.; Sohar, P.; Csampai, A. Synlett 1998, 1193-1194.
29. (b) Polat, T.; Du, Y.; Linhardt, H. J. Synlett 1998, 1195-1196.
30. (c) Buffet, M. F.; Dixon, D. J.; Ley, S. V.; Tate, E. W. Synlett 1998, 1091-1092.
31. (d) Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228.
32. Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
33. (a) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
34. (b) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566.
35. Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843-862.
36. (a) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126.
37. (b) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130.
38. Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. J. Chem. Soc., Chem. Commun. 1998, 2629-2630.
39. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310-5311.
40. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623-9626.
41. For example, application of this sequence to 3,4,5-tri-O-benzyl-D-galactal should allow access to the corresponding C-1-galactals, although we have not yet carried this out.
42. Commercially available from Sigma.
43. Freeman, F.; Robarge, K. D. Carbohydr. Res. 1986, 154, 270-274.
44. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670.
45. Rainier and Allwein (ref 15) have postulated that an excess of reagent is required to compensate for the unfavorable chelation of the active reagent with the ethereal oxygen atoms of the substrate.
46. Armstrong, S. K.; Christie, B. A. Tetrahedron Lett. 1996, 37, 9373-9376.
47. Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264.
48. This second product is not the expected dimer.