
TY  - JOUR
A1  - McKinney, Andrew R. 
A1  - Ridley, Damon D. 
T1  - Synthesis of Equine Metabolites of Anabolic Steroids: Reformatsky Reactions on Estran-17-ones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2002
VL  - 54
IS  - 12
SP  - 757
EP  - 761
KW  - 
UR  - https://doi.org/10.1071/CH01158 
N2  - Reformatsky reactions involving ethyl bromoacetate/zinc are reported for 19-norandrosterone acetate and 19-norepiandrosterone acetate. In each case the major product was the 17&#946;-alcohol from &#945;-attack, although a significant amount of the 17&#945;-alcohol from &#946;-attack was also isolated. The ethyl 3-acetoxy-17&#946;-hydroxy-19-nor-5&#945;,17&#945;-pregnan-21-oates were then hydrolysed to 3,17&#946;-dihydroxy-19-nor-5&#945;,17&#945;-pregnan-21-oic acids or reduced to 19-nor-5&#945;,17&#945;-pregnane-3,17&#946;,21-triols. Comparison of the synthetic products with compounds previously reported as metabolites of norethandrolone in the horse provided valuable information on the regio- and stereo-chemistry of equine steroid metabolism. 
ER  -

