Stereoselective synthesis of (S[hair space])-MPPG, (S)-MTPG and (S[hair space])-(+)-αM4CPG from (R)-4-hydroxyphenylglycine

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

Dawei Ma and Hongqi Tian


Abstract

(R)-4-Hydroxyphenylglycine was protected with a benzyl group and a methyl group was introduced at the α position by using the self-regeneration-of-stereocentre method. After the 4-hydroxy group had been converted into the corresponding trifluoromethanesulfonate (triflate), three palladium-catalyzed reactions were employed to furnish (S[hair space])-α-methyl-4-phosphonophenylglycine [(S[hair space])-MPPG], (S[hair space])-α-methyl-4-(tetrazol-5-yl)phenylglycine [(S[hair space])-MTPG] and (S[hair space])-4-carboxyphenyl-α-methylglycine [(S[hair space])-αM4CPG], a class of new and selective antagonists of metabotropic glutamate receptors.


References

  1. For reviews, see: T. Knopfel, R. Kuhn and H. Allgeier, J. Med. Chem., 1995, 38, 1418 Search PubMed; P. L. Ornstein, D. D. Schoepp and J. A. Monn, Curr. Pharm. Design, 1995, 1, 355; T. Knopfel and F. Gasparini, Drug Discovery Today, 1996, 1, 103 Search PubMed.
  2. J. C. Watkins and G. Collingridge, Trends Pharmacol. Sci., 1994, 15, 333 CrossRef CAS; J.-P. Pin and R. Duvoisin, Neuropharmacology, 1995, 34, 1 CrossRef CAS.
  3. Y. Hayashi, N. Sekiyama, S. Nakanishi, D. E. Jane, D. C. Sunter, E. F. Birse, P. M. Udvarhelyi and J. C. Watkins, J. Neurosci., 1994, 14, 3370 Search PubMed.
  4. D. E. Jane, K. Pittaway, D. C. Sunter, N. K. Thomas and J. C. Watkins, Neuropharmacology, 1995, 34, 851 CrossRef CAS.
  5. J. J. O'Connor, M. J. Rowan and R. Anwyl, Nature, 1994, 367, 557 CrossRef CAS; Z. A. Bortolotto, Z. I. Bashir, C. H. Davies and G. L. Collingridge, Nature, 1994, 368, 740 CrossRef.
  6. D. Ma and H. Tian, Tetrahedron: Asymmetry, 1996, 6, 1567.
  7. E. Wunsch, G. Fries and W. Siedel, Chem. Ber., 1958, 91, 542 CAS.
  8. D. Seebach, J. D. Aebi, R. Neaf and T. Weber, Helv. Chim. Acta, 1985, 68, 144 CrossRef CAS for a review, see: D. Seebach, A. R. Sting and M. Hoffmann, Angew. Chem., Int. Ed. Engl., 1996, 35, 2708 Search PubMed.
  9. N. Sekiyama, Y. Hayashi, S. Nakanishi, D. E. Jane, H.-W. Tse, E. F. Birse and J. C. Watkins, Br. J. Pharmacol., 1996, 117, 1493 Search PubMed and references cited therein.
  10. R. E. Dolle, S. J. Schmidt and L. I. Kruse, J. Chem. Soc., Chem. Commun., 1987, 904 RSC.
  11. X. Lu and J. Zhu, Synthesis, 1987, 726 CrossRef CAS.
  12. N. Chatani and T. Hanafusa, J. Org. Chem., 1986, 51, 4714 CrossRef CAS.
  13. P. L. Ornstein, D. D. Schoepp, M. B. Arnold, J. D. Leander, D. Lodge, J. W. Paschal and T. Elzey, J. Med. Chem., 1991, 34, 90 CrossRef CAS.
  14. S. Cacchi, P. G. Cittini, E. Morera and G. Ortar, Tetrahedron Lett., 1986, 27, 3931 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.