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

被引：10

作者：

Purushottamachar, Puranik ^{[1
,2
]}

Njar, Vincent C. O. ^{[1
,2
,3
]}

机构：

[1] Univ Maryland, Sch Med, Dept Pharmacol, Baltimore, MD 21201 USA

[2] Univ Maryland, Sch Med, Ctr Biomol Therapeut, Rockville, MD 20850 USA

[3] Univ Maryland, Sch Med, Marlene & Stewart Greenebaum Canc Ctr, Baltimore, MD 21201 USA

来源：

STEROIDS | 2012年 / 77卷 / 14期

关键词：

Androgen receptor (AR); 5 alpha-Dihydrotestosterone (DHT); Improved synthetic procedure; Prostate cancer (PC); SELECTIVE REDUCTION; CHEMICAL-SYNTHESIS; PROSTATE; STEROIDS; 5-ALPHA-REDUCTASE; HYDROGENATION; DERIVATIVES; KETONES; AGENTS;

D O I：

10.1016/j.steroids.2012.09.003

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We have devised an efficient procedure for the synthesis of 5 alpha-dihydrotestosterone (DHT) (1) starting from 3 beta-hydroxy-5 alpha-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 beta-[(tert-butyldimethylsilyl)oxy]-5 alpha-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps. (c) 2012 Elsevier Inc. All rights reserved.

引用

页码：1530 / 1534

页数：5

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