
%0 Journal Article
%A McKinney, Andrew R. 
%A Ridley, Damon D. 
%T Synthesis of Equine Metabolites of Anabolic Steroids: Reformatsky Reactions on Estran-17-ones
%J Australian Journal of Chemistry
%D 2002/04/26
%V 54
%N 12
%P 757-761
%K 
%R https://doi.org/10.1071/CH01158
%U https://www.publish.csiro.au/paper/CH01158 
%X 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. 
