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Synthesis of 19‐trideuterated ent ‐testosterone and the GABA A receptor potentiators ent ‐androsterone and ent ‐etiocholanolone
Author(s) -
Komarapuri Shirisha,
Krishnan Kathiresan,
Covey Douglas F.
Publication year - 2008
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1558
Subject(s) - androsterone , chemistry , etiocholanolone , testosterone (patch) , steroid , enantiomer , stereochemistry , endocrinology , biochemistry , hormone , medicine
19‐Trideuteromethyl enantiomers of androgens namely ent ‐testosterone, ent ‐androsterone and ent ‐etiocholanolone were prepared by total synthesis. The isotope labeling at the C‐19 angular methyl group was achieved by using deuterated methyl iodide (99.5% d 3 ) for introduction of C‐19 before closure of the steroid A‐ring. This method yields 19,19,19‐trideuterated steroids without increasing the number of steps involved in the total synthesis of ent ‐androgens. Analysis by mass spectrometry (MS) showed no loss of deuterium during incorporation of C‐19 into ent ‐testosterone. The availability of the compounds will enable these ent ‐androgens to be distinguished by MS from their natural enantiomers in future pharmacokinetic and metabolic studies. Copyright © 2008 John Wiley & Sons, Ltd.