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

•First chemical synthesis of compound 20βOH-NorMD.•Efficient introduction of 17β-hydroxymethyl-17α-methyl substitution pattern.•The crucial Wagner-Meerwein rearrangement is initiated by acidic epoxide opening.

The goal of this work was a good-yielding chemical synthesis of a metandienone metabolite which is of interest in doping analysis. 20βOH-NorMD (IUPAC: 17β-hydroxymethyl-17α-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 20αOH-NorMD has been described before, as was an enzymatic synthesis of 20βOH-NorMD, but no chemical synthesis was published.

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