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

Abstract

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).