Olivanic acid analogues. Part 4. Cycloaddition reactions of p-nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, and synthesis of the 8-oxo-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate system

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1986, Pages 973-981

  Bateson, John H ^a   Southgate, Robert ^a   Tyler, John W ^a   Fell, Stephen C M ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049083506     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19860000973     Document Type: Article

References (33)

1. Part 3, T. C. Smale and R. Southgate, J. Chem. Soc, Perkin Trans. I, 1985, 2235.
2. A. G. Brown, D. F. Corbett, A. J. Eglington, and T. T. Howarth, J. Chem. Soc, Chem. Commun., 1977, 523
3. A. G. Brown, D. F. Corbett, A. J. Eglington, and T. T. Howarth, J. Antibiot., 1979,32,961
4. A. G. Brown, D. F. Corbett, A. J. Eglington, and T. T. Howarth, Tetrahedron, 1983, 39, 2551 and references cited therein.
5. A. J. G. Baxter, K. H. Dickinson, P. M. Roberts, T. C. Smale, and R. Southgate, J. Chem. Soc, Chem. Commun., 1979, 236.
6. J. H. Bateson, A. J. G. Baxter, P. M. Roberts, T. C. Smale, and R. Southgate, J. Chem. Soc. Perkin Trans. 1, 1981, 3242.
7. W. L. Parker, M. L. Rathnum, J. S. Wells, W. H. Trejo, P. S. Principe, and R. B. Sykes, J. Antibiot., 1982, 35, 653.
8. J. H. Bateson, P. M. Roberts, T. C. Smale, and R. Southgate, J. Chem. Soc, Chem. Commun., 1980, 185.
9. J. H. Bateson, R. I. Hickling, P. M. Roberts, T. C. Smale, and R. Southgate, J. Chem. Soc„ Chem. Commun., 1980, 1084.
10. Preliminary communication, J. H. Bateson, D. F. Corbett, and R. Southgate, 'Recent Advances in the Chemistry of P-Lactam Antibiotics,' eds. A. G. Brown and S. M. Roberts, Special Publication No. 52, Royal Society of Chemistry, London, 1985, p. 116.
11. C. L. Branch, S. C. Finch, and M. J. Pearson, Tetrahedron Lett., 1982, 23, 4381 and references cited therein.
12. R. O. Lindsay and C. F. H. Allen, Org. Synth., 1955, Coll. Vol. 3, p. 710.
13. I. Fleming, 'Frontier Orbitals and Organic Chemical Reactions,' Wiley, London, 1976, p. 156
14. R. Huisgen, G. Szeimies, and L. Mobius, Chem. Ber., 1966, 99, 475.
15. J. H. Bateson, A. M. Quinn, T. C. Smale, and R. Southgate, J. Chem. Soc. Perkin Trans. 1, 1985, 2219.
16. R. J. Crawford, A. Mishra, and R. J. Dimmel, J. Am. Chem. Soc, 1966, 88, 3959.
17. S. D. Andrews, A. C. Day, and A. N. McDonald, J. Chem. Soc. C, 1969, 787.
18. D. E. McGreer, N. W. K. Chin, M. G. Vinje, and K. C. K. Wond, Can. J. Chem., 1965, 43, 1407.
19. E. R. Farkas, E. T. Gunda, and J. Cs. Jaszberenyi, Tetrahedron Lett., 1973, 5127.
20. E. T. Gunda, H. Hakli, and J. Cs. Jaszberenyi, Acta. Chem. Scand., Ser. B., 1983, 37, 31.
21. For examples of 0-face direction of reagent in penicillin and cephalosporin sulphoxidations, see R. D. G. Cooper, P. V. Demarco, J. C. Cheng, and N. D. Jones, J. Am. Chem. Soc, 1969, 91, 1408
22. R. D. G. Cooper, P. V. Demarco, C. F. Murphy, and L. A. Spangle, J. Chem. Soc. C, 1970, 340.
23. K. Erdodine-Kover and J. Cs. Jaszberenyi, Org. Magn. Reson., 1984, 22, 552.
24. D. F. Corbett, J. Chem. Soc, Perkin Trans 1, 1986, 421.
25. M. L. Heyman and J. P. Snyder, Tetrahedron Lett., 1973, 2859.
26. J. H. Noggle and R. E. Schirmer, 'The Nuclear Overhauser Effect,' Academic Press, New York, 1971, p. 59.
27. F. Heatley, L. Akhter, and R. T. Brown, J. Chem. Soc, Perkin Trans. 2, 1980, 919.
28. J. D. Mersh and J. K. M. Sanders, Org. Magn. Reson., 1982, 18, 122.
29. B. K. Hunter, L. D. Hall, and J. K. M. Sanders, J. Chem. Soc, Perkin Trans. 1, 1983, 657.
30. K. Mackenzie, 'The Chemistry of the Functional Groups,' ed. S. Patai, 'The Hydrazo, Azo, and Azoxy Groups,' Part 1, Wiley Interscience, London, New York, Sydney, Toronto, 1975, p. 344.
31. R. J. Crawford and A. Mishra, J. Am. Chem. Soc, 1966, 88, 3963.
32. T. C. Clarke, L. A. Wendling, and R. G. Bergmann, J. Am. Chem. Soc, 1977, 99, 2740.
33. K. Tortschanoff, H. Kisch, and O. E. Polansky, Justus Liebigs Ann. Chem., 1975, 449.