First synthesis of a pentadeuterated 3′-hydroxystanozolol-an internal standard in doping analysis

The first synthesis of 16,16,20,20,20-pentadeuterio-3′-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS).