Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite
Literature Information
Publication Date
2018-03-06
DOI
10.1039/C8OB00122G
Impact Factor
3.876
Authors
Nicolas Kratena, Sarah M. Pilz, Matthias Weil, Günter Gmeiner, Valentin S. Enev, Peter Gärtner
View Original
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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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
3-(Methylamino)-1-phenyl-1-propanone hydrochloride (1:1)
CAS Number:
2538-50-3
Molecular Formula:
C10H14ClNO
![1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione structure](https://static.chemtradehub.com/structs/57-/57-96-5-efcc.webp "1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione structure")
1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione
CAS Number:
57-96-5
Molecular Formula:
C23H20N2O3S
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