Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
2027972 | Steroids | 2012 | 5 Pages |
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.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Discovered unprecedented synthesis of 5α-dihydroandrosterone (DHT) in excellent yield. ► Novel procedure will provide easy access to DHT and important starting material for synthesis of novel drug-like compounds. ► Synthetic procedure may be suitable for large-scale industrial production.