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

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• 作者：Puranik Purushottamachar^a ; ^b ; Vincent C.O. Njar^a ; ^b ; ^c ; ^{vnjar@som.umaryland.edu}
• 关键词：AR ; androgen receptor ; BPH ; benign prostate hyperplasia ; DHT ; 5¦Á-dihydrotestosterone ; NMO ; 4-methylmorpholine N-oxide ; PC ; prostate cancer ; T ; testosterone ; TPA ; tetrapropylammonium perruthenate
• 刊名：Steroids
• 出版年：2012
• 出版时间：December, 2012
• 年：2012
• 卷：77
• 期：14
• 页码：1530-1534
• 全文大小：369 K

文摘

We have devised an efficient procedure for the synthesis of 5¦Á-dihydrotestosterone (DHT) (1) starting from 3¦Â-hydroxy-5¦Á-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 17¦Â-[(tert-butyldimethylsilyl)oxy]-5¦Á-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps.