
TY  - JOUR
A1  - McKinney, Andrew R. 
A1  - Ridley, Damon D. 
A1  - Turner, Peter 
T1  - Equine Metabolites of Norethandrolone: Synthesis of a Series of 19-Nor-17&#945;-pregnanediols and 19-Nor-17&#945;-pregnanetriols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2003
VL  - 56
IS  - 8
SP  - 829
EP  - 838
KW  - 
UR  - https://doi.org/10.1071/CH03018 
N2  - A range of 19-nor-17&#945;-pregnanediols and 19-nor-17&#945;-pregnanetriols have been synthesized and used to confirm the structures of major equine urinary metabolites of the synthetic anabolic steroid norethandrolone (1). 19-Nor-5&#945;,17&#945;-pregnane-3&#945;,17&#946;-diol (2), 19-nor-5&#945;,17&#945;-pregnane-3&#946;,17&#946;-diol (4), 19-nor-5&#946;,17&#945;-pregnane-3&#945;,17&#946;-diol (6), and 19-nor-5&#946;,17&#945;-pregnane-3&#946;,17&#946;-diol (7) were prepared by stereoselective reduction of the 3-ene-4-one of norethandrolone. The 19-nor-5&#945;,17&#945;-pregnane-3&#946;,16&#945;,17&#946;-triol (8) and 19-nor-5&#945;,17&#945;-pregnane-3&#946;,16&#946;,17&#946;-triol (9) were prepared from 19-nortestosterone (11) by multistep processes in which the critical step involved Grignard additions to 16-acetoxy-17-ones. The triols (20R)-19-nor-5&#945;,17&#945;-pregnane-3&#946;,17&#946;,20-triol (22) and (20S)-19-nor-5&#945;,17&#945;-pregnane-3&#946;,17&#946;,20-triol (23) were prepared from norethindrone (24) by initial selective A-ring reduction, then subsequent modification of the 17-ethynyl group. By comparison of these compounds with post-administration equine urine samples it was possible to establish A-ring reduction with 3&#946;,5&#945; stereochemistry as well as non-stereospecific 16-hydroxylation and 20-hydroxylation as significant metabolic pathways affecting norethandrolone in the horse. 
ER  -

