Synthesis of 20ßOH-NorMD, a long-term urinary metandienone metabolite

Abstract

The goal of this thesis was a good-yielding chemical synthesis of a metandienone metabolite which is of interest in doping analysis. Compound 20ßOH-NorMD (IUPAC: 17ß-hydroxymethyl-17--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 another isomer: 20-OH-NorMD has been described before by Parr et al.; Zöllner et al. reported a chemoenzymatic way to 20ßOH-NorMD but no chemical synthesis was yet published.