Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

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Abstract

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.

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Kratena, N., Pilz, S. M., Weil, M., Gmeiner, G., Enev, V. S., & Gärtner, P. (2018). Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite. Organic and Biomolecular Chemistry, 16(14), 2508–2521. https://doi.org/10.1039/c8ob00122g

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