Synthesis and analytics of 2,2,3,4,4-d5-19-nor-5alpha-androsterone--an internal standard in doping analysis.
A short and efficient synthesis of pentadeuterated 2,2,3,4,4-d5-19-nor-5alpha-androsterone 7 starting from 19-norandrost-4-ene-3,17-dione 1 by a d1-L-Selectride mediated stereo- and regioselective reduction of the 3-keto group is presented. The use of compound 7 as internal standard for the detection of anabolic steroids via mass spectrometric techniques such as gas chromatography-mass spectrometry (GC-MS) is discussed.
Gaertner
Peter
P
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria. peter.gaertner@tuwien.ac.at
Bica
Katharina
K
Felzmann
Wolfgang
W
Forsdahl
Guro
G
Gmeiner
Günter
G
D045930:Anabolic Agents / Q000032:analysis* / Q000138:chemical synthesis*; D000738:Androsterone / Q000031:analogs & derivatives / Q000032:analysis* / Q000138:chemical synthesis*; D004300:Doping in Sports; D004962:Estranes / Q000032:analysis* / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D012015:Reference Standards
D045930:Anabolic Agents; D004962:Estranes; C036015:19-norandrosterone; D000738:Androsterone