Synthesis and absolute configurations of the naturally occurring 3- and 4-methylmuconolactones: X-ray structures of (S)-1-phenylethylammonium salts and an 8-bromo-1-methyl-muconodilactone

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1996, Pages 2111-2116

  Freer, Andrew A ^a   Kirby, Gordon W ^a   Rao, Ghanakota V ^a   Cain, Ronald B ^b  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748963791     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960002111     Document Type: Article

References (27)

1. R. B. Cain, G. W. Kirby and G. V. Rao, J. Chem. Soc., Chem. Commun., 1989, 1629;
2. B. Chen, G. W. Kirby, G. V. Rao and R. B. Cain, J. Chem. Soc., Perkin Trans. 1, 1996, 1153.
3. D. H. Pieper, K.-H. Engesser, R. H. Don, K. N. Timmis and H.-J. Knackmuss, FEMS Microbiol. Lett., 1985, 29, 63.
4. N. C. Bruce and R. B. Cain, FEMS Microbiol. Lett., 1988, 50, 233;
5. see also D. J. Miller, Zentralbl. Bakteriol. Mikrobiol. Hyg., Abt. 1, Suppl., 1981, 11, 353;
6. F. Rojo, D. H. Pieper, K.-H. Engesser, H.-J. Knackmuss and K. N. Timmis, Science, 1987, 238, 1395.
7. N. C. Bruce, R. B. Cain, D. H. Pieper and K.-H. Engesser, Biochem. J., 1989, 262, 303;
8. D. H. Pieper, K. Stadler-Fritzsche, H.-J. Knackmuss, K. H. Engesser, N. C. Bruce and R. B. Cain, Biochem. J., 1990, 271, 529.
9. J. A. Elvidge, R. P. Linstead and P. Sims, J. Chem. Soc., 1951, 3386 and citations therein.
10. Preliminary communication, R. B. Cain, A. A. Freer, G. W. Kirby and G. V. Rao, J. Chem. Soc., Perkin Trans. 1, 1989, 202.
11. E. F. Ahlquist and R. B. Cain, unpublished observations;
12. E. F. Ahlquist, Ph.D. Thesis, University of Kent at Canterbury, 1977.
13. J. A. Elvidge, R. P. Linstead and P. Sims, J. Chem. Soc., 1951, 3398.
14. D. Catelani, A. Fiecchi and E. Galli, Biochem. J., 1971, 121, 89.
15. H.-J. Knackmuss, M. Hellwig, H. Lackner and W. Otting, Eur. J. Appl. Microbiol., 1976, 2, 267.
16. J. B. Powlowski and S. Dagley, J. Bacteriol., 1985, 163, 1126.
17. R. V. J. Chari, C. P. Whitman, J. W. Kozarich, K.-L. Ngai and L. N. Ornston, J. Am. Chem. Soc., 1987, 109, 5514.
18. G. W. Kirby, G. J. O'Loughlin and D. J. Robins, J. Chem. Soc., Chem. Commun., 1975, 402;
19. J. Chem. Soc., Perkin Trans. 1, 1993, 1967.
20. G. Avigad and S. Englard, Fed. Proc., 1969, 28, 345.
21. R. B. Cain, B. Chen, G. W. Kirby and G. V. Rao, unpublished observations.
22. A. T. Ainsworth and G. W. Kirby, J. Chem. Soc. (C), 1968, 1483.
23. E. Schmidt, G. Remberg and H.-J. Knackmuss, Biochem. J., 1980, 192, 331.
24. J. A. Gerlt and P. G. Gassmann, J. Am. Chem. Soc., 1992, 114, 5928.
25. K.-L. Ngai and R. G. Kallen, Biochemistry, 1983, 22, 5231.
26. D. Rodgers, Acta Crystallogr., Sect. A, 1981, 37, 734.
27. C. J. Gilmore, J. Appl. Crystallogr., 1984, 17, 42.