New metabolites from toluene dioxygenase dihydroxylation of oxygenated biphenyls

Tetrahedron Asymmetry

Volumn 8, Issue 7, 1997, Pages 975-977

  Gonzalez, David ^a   Schapiro, Valeria ^b   Seoane, Gustavo ^b   Hudlicky, Tomas ^a  

^a University of Florida ^*  (United States)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; CYCLOHEXANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG IDENTIFICATION; DRUG SYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE EXPRESSION; GENE TRANSFER; OXIDATION; PRIORITY JOURNAL; PSEUDOMONAS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030951756     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00059-1     Document Type: Article

References (22)

1. (a) Ziffer, H.; Kabuto, K.; Gibson, D. T.; Kobal, V. M.; Jerina, D. M. Tetrahedron 1977, 33, 2491;
2. (b) Gibson, D. T.; Roberts, R. L.; Wells, M. C.; Kobal, V. M. Biochem. Biophys. Res. Commun. 1973, 50, 211;
3. (c) Catelani, D.; Sorlini, C.; Treccani, V. Experientia 1971, 27, 1173.
4. (a) Safe, S.H. in Microbial Degradations of Organic Compounds Gibson, D. T., Ed., Marcel Dekker, New York, 1984, 361;
5. (b) Furukawa, K.; Tomizuka, N.; Kamibayashi, A. Appl. Environ. Microbiol. 1979, 38, 301.
6. Kimura, K.; Kato, H.; Nishi, A.; Furukawa, K. Biosci. Biotech. Biochem. 1996, 60, 220.
7. Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T., Abboud, K. J. Org. Chem. 1997, 62, 1194.
8. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. Organic Synthesis: Theory and Applications Hudlicky, T., Ed., JAI Press, Greenwich, CT, 1993, 2, 113;
9. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chimica Acta 1990, 8, 3;
10. (c) Carless, H. A. J. Tetrahedron: Asymm. 1992, 3, 795;
11. (d) Hudlicky, T.; Reed, J. W. in Advances in Asymmetric Synthesis Hassner, A., Ed., JAI Press, Greenwich, CT, 1995, 271;
12. (e) Hudlicky, T. in Green Chemistry: Designing Chemistry for the Enviroment, ACS Symposium Series Anastas, P. T.; Williamson, T., Eds., Washington, DC, 1996, 626, 180;
13. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem Commun. 1996, 1993;
14. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3;
15. (h) Hudlicky, T; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195;
16. (i) Grund, A. D. SIM News 1995, 45, 59.
17. Zylstra, G. J.; Gibson D. T. J. Biol. Chem. 1989, 264, 14940.
18. 4, and the solvent was evaporated at 20°C. The crude diol was purified via flash chromatography on deactivated silica gel (10% water) using hexane/ethyl acetate (7:3) as the eluent to render in each case a pure compound: diol 1 (3 g/L), diol 2 (2.5 g/L), and diol 3 (0.8 g/L).
19. Ley, S. V.; Redgrave, A. J.; Taylor, S. C.; Ahmed, S.; Ribbons, D. W. Synlett 1991, 741.
20. Boyd, D. R.; Hand, M. V.; Sharma, N. D.; Chima, J.; Dalton, H.; Sheldrake, G. N. J. Chem. Soc., Chem. Commun. 1991, 1631.
21. 3: 220.1099. Found: 220.1098.
22. 4: 250.1205. Found: 250.1205.