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Steroids. 2012 Dec;77(14):1530-4. doi: 10.1016/j.steroids.2012.09.003. Epub 2012 Oct 5.

A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist.

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  • 1Department of Pharmacology, University of Maryland School of Medicine, Baltimore, MD 21201-1559, USA.

Abstract

We have devised an efficient procedure for the synthesis of 5α-dihydrotestosterone (DHT) (1) starting from 3β-hydroxy-5α-androstan-17-one, providing the product in unprecedented 82% yield. A reported method of using toxic Jones reagent is replaced by milder oxidizing agent (NMO/TPAP) in the synthesis of a key intermediate 17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps.

Copyright © 2012 Elsevier Inc. All rights reserved.

PMID:
23044354
[PubMed - indexed for MEDLINE]
PMCID:
PMC3959746
Free PMC Article
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