Cross-metathesis of C-glycosides and peptides

Synthetic Communications

Volumn 37, Issue 16, 2007, Pages 2757-2769

  Brüchner, Peter ^a   Koch, David ^a   Voigtmann, Ulrike ^b   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b BAYER PHARMA AG   (Germany)

Author keywords

C glycopeptides; Cross metathesis; Posttranslational synthesis

Indexed keywords

ACRYLAMIDE DERIVATIVE; ALKENE; C GLYCOSIDE DERIVATIVE; GLYCOSIDE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DIMERIZATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; RING CLOSING METATHESIS;

EID: 34547936884     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701481146     Document Type: Article

References (40)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130;
2. (b) Dwek, R. A. Chem. Rev. 1996, 3, 683-720;
3. (c) Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370-2376;
4. (d) Bertozzi, C. R.; Kiessling, L. L. Science 2002, 291, 2357-2364;
5. (e) Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. Bioorg. Med. Chem. Lett. 2005, 105, 425-448.
6. (a) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422;
7. (b) Chambers, D. J.; Evans, G. R.; Fairbanks, A. J. Tetrahedron Asymmetry 2005, 16, 45-55;
8. (c) Chaulagain, M. R.; Postema, M. H. D.; Valerioteb, F.; Pietraszkewicz, H. Tetrahedron Lett. 2004, 45, 7791-7794.
9. (a) Connon, S. J.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900-1923;
10. (b) Vernall, A. J.; Abell, A. D. Adrichim. Acta 2003, 36, 93-105;
11. (c) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
12. Vernall, A. J.; Abell, A. D. Org. Biomol. Chem. 2004, 2, 2555-2557.
13. Garvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594.
14. (a) Wan, Q.; Cho, Y. S.; Lambert, T. H.; Danishefsky, S. J. J. Carbohydr. Chem. 2005, 24, 425-440;
15. (b) Dondoni, A.; Giovannini, P. P.; Perone, D. J. Org. Chem. 2005, 70, 5508-5518;
16. (c) Nolen, E. G.; Kurish, A. J.; Potter, J. M.; Donahue, L. A.; Orlando, M. D. Org. Lett. 2005, 7, 3383-3386;
17. (d) Schmidtmann, F. W.; Benedum, T. E.; McGarvey, G. J. Tetrahedron Lett. 2005, 46, 4677-4681;
18. (e) Liu, S.; Ben, R. N. Org. Lett. 2005, 7, 2385-2388;
19. (f ) Postema, M. H. D. Org. Lett. 2003, 5, 1721-1723;
20. (g) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449-2453;
21. (h) Godin, G.; Compain, P.; Martin, O. R. Org. Lett. 2003, 5, 3269-3272;
22. (i) Biswas, K.; Coltart, D. M.; Danyshefsky, S. Tetrahedron Lett. 2002, 43, 6107-6110;
23. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 19, 2380-2388;
24. (l) Dominique, R.; Liu, B.; Das, S.; Roy, R. Synthesis 2000, 862-868.
25. Hu, Y. J.; Roy, R. Tetrahedron Lett. 1999, 40, 3305-3308.
26. Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. 1 1998, 2485-2500.
27. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
28. (a) Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Syn. Lett. 2001, 430-432;
29. (b) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 634, 216-222;
30. (c) Cossy, J.; BouzBouz, S. Org. Lett. 2001, 3, 1451-1454;
31. (d) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784.
32. Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002, 12, 1873-1876.
33. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179;
34. (b) Gesslar, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
35. (a) Imhof, S.; Randl, S.; Blechert, S. Chem. Commun. 2001, 1692-1693;
36. (b) Randl, S.; Connon, S. J.; Blechert, S. Chem. Commun. 2001, 1796-1797.
37. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
38. Grubbs, R. H. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH, 2003.
39. For coordination of Trp moieties to transition metals, see Kaminskaia, N. V.; Ullmann, G. M.; Fulton, D. B.; Kostic, N. M. Inorg. Chem. 2000, 39, 5004-5013.
40. Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209-2212.