New arene cis-dihydrodiol metabolites from β-bromostyrenes

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2067-2069

  Novak, Bennett H ^a   Hudlicky, Tomas ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA BROMOSTYRENE DIOL; OXYGENASE; POLYCYCLIC AROMATIC HYDROCARBON; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; ESCHERICHIA COLI; FERMENTATION; METABOLITE; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033522722     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00237-2     Document Type: Article

References (31)

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21. The following styrene-related metabolites have been identified: o-bromostyrene: Konigsberger, K.; Hudlicky, T. Tetrahedron: Asymmetry 1993, 4, 2469; Ref. 3a,b; bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L. Tetrahedron: Asymmetry 1995, 6, 537; o-bromo bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L.; Butora, G.; Gum, A. G.; Fernley, S. P.; Thorpe, A. J.; Ellis, M. R. Chirality 1995, 7, 556.
22. The following styrene-related metabolites have been identified: o-bromostyrene: Konigsberger, K.; Hudlicky, T. Tetrahedron: Asymmetry 1993, 4, 2469; Ref. 3a,b; bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L. Tetrahedron: Asymmetry 1995, 6, 537; o-bromo bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L.; Butora, G.; Gum, A. G.; Fernley, S. P.; Thorpe, A. J.; Ellis, M. R. Chirality 1995, 7, 556.
23. The following styrene-related metabolites have been identified: o-bromostyrene: Konigsberger, K.; Hudlicky, T. Tetrahedron: Asymmetry 1993, 4, 2469; Ref. 3a,b; bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L. Tetrahedron: Asymmetry 1995, 6, 537; o-bromo bromoethylbenzene: Stabile, M. R.; Hudlicky, T.; Meisels, M. L.; Butora, G.; Gum, A. G.; Fernley, S. P.; Thorpe, A. J.; Ellis, M. R. Chirality 1995, 7, 556.
24. (a) Hudlicky, T.; Boros, C. H.; Boros, E. E. Synthesis 1992, 174;
25. (b) Butora, G.; Hudlicky, T.; Fernley, S. P.; Stabile, M. R.; Gum, A. G.; Gonzalez, D. Synthesis 1998, 665;
26. (c) Hudlicky, T.; Butora, G.; Gum, A. G.; Abboud, K. A. Synthesis 1998, 275.
27. 3) δ 136.4, 135.8, 132.2, 124.8, 124.0, 108.1, 70.0, 66.6.
28. The fermentations were carried out as described previously (Refs. 3a, 6a) in a 12 L fermentor using IPTG as the inducer. Hudlicky, T.; Stabile, M. R.; Gibson, D. T.; Whited, G. M. Org. Synth. 1999, 76, 77.
29. 3).
30. 2O: C, 65.10; H, 9.97; found: C, 65.21; H, 9.56.
31. Hudlicky, T.; Boros, C. H. Tetrahedron Lett. 1993, 34, 2557.