Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

The human urinary long-term metabolite "M3" (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrost-13-en-3-ol) of the common doping agent DHCMT has thus far been detected via GC/MS-MS, creating ambiguities concerning its absolute configuration. Its structure was elucidated via the synthesis...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (14), p.2508-2521
Main Authors: Kratena, Nicolas, Pilz, Sarah M, Weil, Matthias, Gmeiner, Günter, Enev, Valentin S, Gärtner, Peter
Format: Article
Language:English
Subjects:
Absolute configuration
Configurations
Stereoisomerism
Stereoisomers
Synthesis
Testosterone - analogs & derivatives
Testosterone - chemical synthesis
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Summary:The human urinary long-term metabolite "M3" (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrost-13-en-3-ol) of the common doping agent DHCMT has thus far been detected via GC/MS-MS, creating ambiguities concerning its absolute configuration. Its structure was elucidated via the synthesis of all eight possible stereoisomers with 17β-hydroxymethyl configuration. The highlights of the synthesis consist of a novel first generation approach to 4β-chloro-5β compounds as well as a divergent route which allows easy access to the remaining A-ring chlorohydrins.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00122g