Synthesis of 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one: a long-term metandienone metabolite

Abstract

The goal of this work was a good-yielding chemical synthesis of a metandienone metabolite which is of interest in doping analysis. 20bOH-NorMD (IUPAC: 17b-hydroxymethyl-17a-methyl-18-norandrosta-1,4,13-triene-3-one) has been identified as a long-term urinary metabolite which can be detected and attributed to metandienone up to almost 3 weeks after exposure. The chemical synthesis of its epimer 20aOH-NorMD has been described before, as was an enzymatic synthesis of 20bOH-NorMD, but no chemical synthesis was published