title: A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist.
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.
authors.affiliation: Department of Pharmacology, University of Maryland School of Medicine, Baltimore, MD 21201-1559, USA.
authors.forename: Puranik
authors.initials: P
authors.lastname: Purushottamachar
authors.forename: Vincent C O
authors.initials: VC
authors.lastname: Njar
mesh_terms: D000728:Androgens / Q000138:chemical synthesis* / Q000737:chemistry; D000738:Androsterone / Q000031:analogs & derivatives / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry; D013196:Dihydrotestosterone / Q000138:chemical synthesis* / Q000737:chemistry; D009025:Morpholines / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D000728:Androgens; D003497:Cyclic N-Oxides; D009025:Morpholines; D013196:Dihydrotestosterone; C067960:4-methylmorpholine N-oxide; D000738:Androsterone; C561866:3-hydroxyandrost-1-en-17-one