Two free radical routes for the preparation of novel difluoromethylene-linked serine-O-glycopeptide analogues

(Note: The full text of this document is currently only available in the PDF Version )

Timothée F. Herpin, William B. Motherwell and Jean-Marc Weibel


Abstract

The first examples of gem-difluoromethylene-linked analogues of serine-derived glycopeptides have been prepared in a highly stereoselective manner using two complementary free radical chain reactions.


References

  1. H. Lis and N. Sharon, Eur. J. Biochem., 1993, 218, 1 CAS.
  2. J. Montreuil, in Comprhensive Biochemistry, ed. A. Neuberger and L. L. van Deene, Elsevier, Amsterdam, 1982, vol. 19 BII, 1 Search PubMed.
  3. J. F. Fisher, A. W. Harrison, G. L. Bundy, K. F. Wilkinson, B. D. Rush and M. J. Ruwart, J. Med. Chem., 1991, 34, 3141.
  4. G. Rassu, F. Zanardi, L. Battistini and G. Casiraghi, Tetrahedron: Asymmetry, 1995, 6, 371 CrossRef CAS.
  5. L. Colombo, G. Casiraghi and A. Pattalis, J. Org. Chem., 1991, 56, 3897 CrossRef CAS.
  6. G. Casiraghi, L. Colombo, G. Rassu and P. Spanu, J. Org. Chem., 1991, 56, 6523 CrossRef CAS.
  7. P. Garner and J. M. Park, J. Org. Chem., 1990, 55, 3772 CrossRef CAS.
  8. A. G. M. Barrett and S. A. Lebold, J. Org. Chem., 1990, 55, 3853 CrossRef CAS.
  9. C. R. Bertozzi, P. D. Hoepricht and M. D. Berdnarski, J. Org. Chem., 1992, 57, 6092 CrossRef CAS.
  10. M. K. Gurjar, A. S. Mainkar and M. Syamala, Tetrahedron: Asymmetry, 1993, 4, 2343 CrossRef CAS.
  11. G. Simchen and E. Pürkner, Synthesis, 1990, 524.
  12. H. Kessler, V. Wittmann, M. Köck and M. Kottenhahn, Angew. Chem., Int. Ed. Engl., 1992, 31, 902 CrossRef.
  13. J. R. Axon and A. L. J. Beckwith, J. Chem. Soc., Chem. Commun., 1995, 549 RSC.
  14. B. Giese, Angew. Chem., Int. Ed. Engl., 1989, 28, 969 CrossRef.
  15. G. M. Blackburn, Chem. Ind. (London), 1981, 134 CAS; G. M. Blackburn, D. E. Kent and F. Kolkmann, J. Chem. Soc., Perkin Trans., 1984, 1119 Search PubMed; R. D. Chambers, R. Jaouhari and D. O'Hagen, Tetrahedron, 1989, 45, 5101 CrossRef CAS.
  16. J. S. Houlton, W. B. Motherwell, B. C. Ross, M. J. Tozer, D. J. Williams and A. M. Z. Slawin, Tetrahedron, 1993, 49, 8087 CrossRef CAS.
  17. T. F. Herpin, W. B. Motherwell and M. J. Tozer, Tetrahedron: Asymmetry, 1994, 5, 2269 CrossRef CAS.
  18. W. B. Motherwell, B. C. Ross and M. J. Tozer, Synlett, 1989, 68 CrossRef CAS.
  19. J. A. Bajgrowicz, A. El Hallaoui, R. Jacquier, C. Pigierre and P. Viallefont, Tetrahedron, 1985, 41, 1833 CrossRef CAS.
  20. R. F. W. Jackson, N. Wishart, A. Wood, K. James and M. J. Wythes, J. Org. Chem., 1992, 57, 3397 CrossRef CAS.
  21. J. E. Baldwin, R. E. Adlington, D. J. Birch, J. A. Crawford and J. B. Sweeney, J. Chem. Soc., Chem. Commun., 1986, 1339 RSC.
  22. J. E. Baldwin, R. Fieldhouse and A. T. Russel, Tetrahedron Lett., 1993, 34, 5491 CrossRef CAS.
  23. K. Burger, H. Neuhauser and M. Rudolph, Chem.-Ztg., 1990, 114, 249 Search PubMed.
  24. K. Burger, M. Gold, H. Neuhauser and M. Rudolph, Chem.-Ztg., 1991, 115, 77 Search PubMed.
  25. D. H. R. Barton, Y. Hervé, P. Potier and J. Thierry, Tetrahedron, 1988, 44, 5479 CrossRef CAS; D. H. R. Barton, D. Crich and W. B. Motherwell, Tetrahedron, 1985, 41, 3901 CrossRef CAS.
  26. D. H. R. Barton, S. D. Gero, Quiclet-Sire and M. Samadi, Tetrahedron: Asymmetry, 1994, 5, 2123 CrossRef CAS.
  27. A. L. J. Beckwith, S. G. Pyne, B. Dikic, C. L. L. Chai, P. A. Gordon, B. W. Skelton, M. J. Tozer and A. H. White, Aust J. Chem., 1993, 46, 1425 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.