Equine metabolites of norethandrolone: Synthesis of a series of 19-nor-17α-pregnanediols and 19-nor-17α-pregnanetriols

Australian Journal of Chemistry

Volumn 56, Issue 8, 2003, Pages 829-838

  McKinney, Andrew R ^a,b   Ridley, Damon D ^a   Turner, Peter ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b Australian Racing Forensic Lab   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL MODIFICATION; HYDROXYLATION; REDUCTION; STEREOCHEMISTRY; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

ANABOLIC STEROID; NORETHANDROLONE; STEREOSELECTIVE REDUCTION;

ORGANIC COMPOUNDS;

EID: 0042515255     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH03018     Document Type: Article

References (38)

1. A. R. McKinney, D. D. Ridley, C. J. Suann, J. Mass Spectrom. 2001, 36, 145.
2. (a) E. Houghton, M. C. Dumasia, Xenobiotica 1979, 9, 269.
3. (b) M. C. Dumasia, E. Houghton, Xenobiotica 1981, 11, 323.
4. (a) M. C. Dumasia, E. Houghton, Xenobiotica 1984, 14, 647.
5. (a) S. M. R. Stanley, L. Smith, J. P. Rodgers, J. Chromatogr. B: Biomed. Sci. Appl. 1997, 690, 55.
6. C. J. W. Brooks, A. R. Thawley, P. Rocher, B. S. Middleditch, G. M. Anthony, W. G. Stillwell, J. Chromatogr. Sci. 1971, 9, 35.
7. (a) E. Houghton, M. C. Dumasia, Xenobiotica 1980, 10, 381.
8. (b) W. M. Mück, J. D. Henion, Biomed. Environ. Mass Spectrom. 1990, 19, 37.
9. (c) C. Schoene, A. N. R. Nedderman, E. Houghton, Analyst 1994, 119, 2537.
10. (d) S. M. R. Stanley, S. Kent, J. P. Rodgers, J. Chromatogr. B: Biomed. Sci. Appl. 1997, 704, 119.
11. R. J. Ward, A. M. Lawson, C. H. Shackleton, J. Steroid Biochem. 1977, 8, 1057.
12. A. R. McKinney, D. D. Ridley, C. J. Suann, Aust. J. Chem. 2001, 54, 757.
13. A. Bowers, H. J. Ringold, E. Denot, J. Am. Chem. Soc. 1958, 80, 6115.
14. R. B. Gabbard, A. Segaloff, J. Org. Chem. 1962, 27, 655.
15. N. S. Leeds, D. K. Fukushima, T. F. Gallagher, J. Am. Chem. Soc. 1954, 76, 2943.
16. W. S. Johnson, B. Gastambide, R. Pappo, J. Am. Chem. Soc. 1957, 79, 1991.
17. D. Menberu, P. V. Nguyen, K. D. Onan, P. W. Le Quesne, J. Org. Chem. 1992, 57, 2100.
18. H. J. Liu, I. S. Han, Synth. Comm. 1985, 15, 759.
19. T. Nambara, K. Shimada, S. Iwamura, M. Mori, M. Nokubo, Chem. Pharm. Bull. 1973, 21, 2474.
20. M. G. Combe, W. A. Denny, G. D. Meakins, Y. Morisawa, J. Chem. Soc. C 1971, 2300.
21. P. Canonne, G. B. Foscolos, Tetrahedron Lett. 1979, 45, 4383.
22. R. Hamelin, Bull. Soc. Chim. Fr. 1961, 915.
23. (a) T. Takegoshi, Chem. Pharm. Bull. 1972, 20, 1260.
24. (b) W. Schänze, G. Opfermann, M. Donike, J. Steroid Biochem. 1990, 36, 153.
25. (a) P. O. Edlund, L. Bowers, J. Henion, J. Chromatogr. 1989, 487, 341.
26. (b) H. Bi, R. Massé, J. Steroid Biochem. Mol. Biol. 1992, 42, 533.
27. I. Salamon, T. Reichstein, Helv. Chim. Acta 1947, 30, 1616.
28. L. Schor, A. M. Seldes, E. G. Gros, J. Chem. Soc., Perkin Trans. 1 1990, 163.
29. R. E. Counsell, U. S. Pat. 3,014,935 1961.
30. R. T. Rapala, E. Farkas, J. Am. Chem. Soc. 1958, 80. 1008.
31. R. A. Johnson, G. L. Bundy, G. A. Youngdale, D. R. Morton, Int. Pat. WO 87/02367 1987.
32. D. K. Fukushima, S. Dobriner, J. Org. Chem. 1961, 26, 3022.
33. SAINT and XPREP 1995 (Bruker: Madison, WI).
34. teXsan for Windows: Single Crystal Structure Analysis Software 1998 (Molecular Structure Corp.: The Woodlands, TX).
35. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
36. Xtal3. 6 (Eds S. R. Hall, D. J. du Boulay, R. Olthof-Hazekamp) 1999 (University of Western Australia: Perth).
37. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
38. G. M. Sheldrick, SHELXL-97 1997 (University of Göttingen: Göttingen).