Short, stereoselective synthesis of C-glycosyl asparagines via an olefin cross-metathesis

Tetrahedron Letters

Volumn 44, Issue 12, 2003, Pages 2449-2453

  Nolen, Ernest G ^a   Kurish, Adam J ^a   Wong, Kelli A ^a   Orlando, Michael D ^a  

^a Center for Language and Brain   (United States)

Author keywords

C allyl glycoside; C glycosyl amino acid; C glycosyl asparagine; Cross metathesis; Vinyl glycines

Indexed keywords

ALKENE; ASPARAGINE DERIVATIVE; GLYCINE DERIVATIVE; GLYCOSIDE; VINYL DERIVATIVE;

ARTICLE; CATALYST; HYDROGENATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037450989     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00350-2     Document Type: Article

References (33)

1. Glycoproteins and Human Disease; Brockhausen, I.; Kuhns, W., Ed.; Chapman and Hall: New York, 1997.
2. Bertozzi C.R., Kiessling L.L. Science. 291:2001;2357-2364.
3. Rudd P.M., Elliott T., Cresswell P., Wilson I.A., Dwek R.A. Science. 291:2001;2370-2376.
4. Allen J.R., Danishefsky S.J. J. Am. Chem. Soc. 121:1999;10875-10882.
5. Nagy J.O., Wang P., Gilbert J.H., Schaefer M.E., Hill T.G., Callstrom M.R., Bednarski M.D. J. Med. Chem. 35:1992;4501-4502.
6. Lundquist J.J., Toone E.J. Chem. Rev. 102:2002;555-578.
7. Dondoni A., Marra A. Chem. Rev. 100:2000;4395-4422.
8. Paterson D.E., Griffin F.K., Alcaraz M.-L., Taylor R.J.K. Eur. J. Org. Chem. 2002;1323-1336.
9. Dondoni A., Mariotti G., Marra A. J. Org. Chem. 67:2002;4475-4486.
10. Dondoni A., Mariotti G., Marra A., Massi A. Synthesis. 2001;2129-2137.
11. Nolen E.G., Watts M.M., Fowler D.J. Org. Lett. 4:2002;3963-3965.
12. Vincent S.P., Schleyer A., Wong C.-H. J. Org. Chem. 65:2000;4440-4443.
13. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953-956.
14. Biswas K., Coltart D.M., Danishefsky S.J. Tetrahedron Lett. 43:2002;6107-6110.
15. Dominique R., Das S.K., Roy R. Chem. Commun. 1998;2437-2438.
16. Dominique R., Liu B., Das S.K., Roy R. Synthesis. 2000;862-868.
17. Dominique R., Roy R. Tetrahedron Lett. 43:2002;395-398.
18. (a) Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., Grubbs R.H. J. Am. Chem. Soc. 122:2000;58-71; (b) See Ref. 9d; (c) Postema M.H.D., Piper J.L. Tetrahedron Lett. 43:2002;7095-7099.
19. (a) Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., Grubbs R.H. J. Am. Chem. Soc. 122:2000;58-71; (b) See Ref. 9d; (c) Postema M.H.D., Piper J.L. Tetrahedron Lett. 43:2002;7095-7099.
20. Dondoni A., Giovannini P.P., Marra A. J. Chem. Soc., Perkin Trans. 1. 2001;2380-2388.
21. McGarvey G.J., Benedum T.E., Schmidtmann F.W. Org. Lett. 4:2002;3591-3594.
22. Roe B.A., Boojamra C.G., Griggs J.L., Bertozzi C.R. J. Org. Chem. 61:1996;6442-6445.
23. Afzali-Ardakani A., Rapoport H. J. Org. Chem. 45:1980;4817-4820.
24. Tashiro T., Fushiya S., Nozoe S. Chem. Pharm. Bull. 36:1988;893-901.
25. Hanessian S., Sahoo S.P. Tetrahedron Lett. 25:1984;1425-1428.
26. 4) m/z.
27. Cadot C., Dalko P.I., Cossy J. Tetrahedron Lett. 43:2002;1839-1841.
28. Maishal T.K., Sinha-Mahapatra D.K., Paranjape K., Sarkar A. Tetrahedron Lett. 43:2002;2263-2267.
29. Basu K., Cabral J.A., Paquette L.A. Tetrahedron Lett. 43:2002;5453-5456.
30. Chatterjee A.K., Grubbs R.H. Org. Lett. 1:1999;1751-1753.
31. Debenham S.D., Debenham J.S., Burk M.J., Toone E.J. J. Am. Chem. Soc. 119:1997;9897-9898.
32. Zhu Y.-F., Yamazaki T., Tsang J.W., Lok S., Goodman M. J. Org. Chem. 57:1992;1074-1081.
33. Sakaitani M., Hori K., Ohfune Y. Tetrahedron Lett. 29:1988;2983-2984.