Pyrrolidinones derived from (S)-pyroglutamic acid. Part 2. Conformationally constrained kainoid analogues

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 16, 2000, Pages 2793-2804

  Dyer, James ^a   King, Amanda ^a   Keeling, Steve ^b   Moloney, Mark G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHROMATOGRAPHY; EVAPORATION; SOLUTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

REMOTE SUBSTITUENTS; RING CONFORMATION;

AROMATIC HYDROCARBONS;

EID: 0034699185     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002001j     Document Type: Article

References (24)

1. For Part 1, see J. H. Bailey, D. T. Cherry, J. Dyer, M. G. Moloney, M. J. Bamford, S. Keeling and R. B. Lamont, J. Chem. Soc., Perkin Trans, 1, 2000, preceding paper (DOT: 10.1039/b001999m).
2. J. Dyer, S. Keeling and M. G. Moloney, Chem. Commun., 1998, 461.
3. M. G. Moloney, Nat. Prod. Rep., 1999, 16, 485.
4. M. G. Moloney, Nat. Prod. Rep., 1998, 15, 205.
5. M.-R. Schneider, P. Klotz, I. Ungureanu, A. Mann and C.-G. Wermuth, Tetrahedron Lett., 1999, 40, 3873.
6. M. V. Chevliakov and J. Montgomery, Angew. Chem., Int. Ed., 1998, 37, 3144.
7. P. Barraclough, P. Hudhomme, C. A. Spray and D. W. Young, Tetrahedron, 1995, 51, 4195.
8. J. S. Bryans, J. M. Large and A. F. Parsons, J. Chem. Soc., Perkin Trans, 1, 1999, 2905.
9. J. S. Bryans, J. M. Large and A. F. Parsons, J. Chem. Soc., Perkin Trans, 1, 1999, 2897.
10. M. D. Fletcher and M. M. Campbell, Chem. Rev., 1998, 98, 763.
11. A. Dutta, in Specialist Periodical Reports, Amino acids, Peptides and Proteins, ed. J. S. Davies, Royal Society of Chemistry, Cambridge, 1998.
12. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart and W. D. Lubell, Tetrahedron, 1997, 53, 12789.
13. J. Gante, Angew: Chem., Int. Ed. Engl., 1994, 33, 1699.
14. M. J. Beard, J. H. Bailey, D. T. Cherry, M. G. Moloney, S. B. Shim, K. Statham, M. Bamford and R. B. Lamont, Tetrahedron, 1996, 52, 3719.
15. J. T. Pinhey, in Comprehensive Organometallic Chemistry II, ed. A. McKillop, Pergamon, Oxford, 1995, vol. 11.
16. J. T. Pinhey, Aust. J. Chem., 1991, 44, 1353.
17. G. M. Rubottom, in Oxidation in Organic Chemistry, ed. W. H. Trahanovsky, Academic, London, 1982, ch. 1.
18. V. Soloshonok, C. Cai, V. J. Hruby and L. V. Meervelt, Tetrahedron, 1999, 55, 12045.
19. Structures optimised with Spartan® (3-21G or PM3 semi-empirical basis set in the gas phase) or Chem 3D Pro 3.5 (PM3 basis set).
20. J. H. Bailey, D. T. Cherry, K. M. Crapnell, M. G. Moloney, S. B. Shim, M. Bamford and R. B. Lamont, Tetrahedron, 1997, 53, 11731.
21. H. C. Bell, J. R. Kalman, J. T. Pinhey and S. Sternhell, Aust. J. Chem., 1979, 32, 1521.
22. D. I. McGee and M. Ramaseshan, Synlett, 1994, 743.
23. A. F. Abdel-Magid, B. D. Harris and C. A. Maryanoff, Synlett, 1994, 81.
24. D. A. Fletcher, R. F. McMeeking and D. Parkin, J. Chem. Inf. Comput. Sci., 1996, 36, 746.