IMPROVED SYNTHESES OF EPRISTERIDE, A POTENT HUMAN 5-ALPHA-REDUCTASE INHIBITOR

被引：13
|
作者：
BAINE, NH
OWINGS, FF
KLINE, DN
RESNICK, T
PING, LJ
FOX, M
MEWSHAW, RE
TICKNER, AM
KOWALSKI, CJ
机构：
[1] Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, UW-2810, Pennsylvania 19406-2799, 709 Swedeland Road, King of Prussia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期
关键词：
D O I：
10.1021/jo00099a031
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two improved syntheses of a potent human 5 alpha-reductase inhibitor, epristeride, SK&F 105657, are described. The first synthesis starts from methyl 3-oxoandrost-4-ene-17 beta-carboxylate (1), which is converted to epristeride (5) in four synthetic steps in 44% overall yield. The second synthesis starts from commercially available 3-oxoandrost-4-en-17 beta-carboxylic acid (7), which is converted to epristeride (5) in two synthetic steps in 63% overall yield. Both syntheses are suitable for large scale production and have been employed to produce kilograms supplies of epristeride in high purity.
引用
收藏
页码：5987 / 5989
页数：3
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