ON THE REGIOSELECTIVITY OF SH-CONTAINING NUCLEOPHILES TOWARDS ANDROSTA-1,4-DIENE-3,17-DIONE, A PRECURSOR FOR BIOLOGICALLY-ACTIVE STEROIDS

被引:0
作者
MULLER, A [1 ]
WEISS, D [1 ]
BECKERT, R [1 ]
机构
[1] FRIEDRICH SCHILLER UNIV,INST ORGAN & MAKROMOLEK CHEM,HUMBOLDTSTR 10,O-6900 JENA,GERMANY
来源
LIEBIGS ANNALEN DER CHEMIE | 1993年 / 01期
关键词
ANDROSTA-1,4-DIENE-3,17-DIONE; THIOKETALS; HEMITHIOKETALS; STEROIDS; MICHAEL ADDITION; DOUBLE;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thioketals have been prepared from androsta-1,4-diene-3,17-dione (1) and SH-containing compounds in the presence of different catalysts. The thioketals 4 are obtained by using the aromatic thiols 3d, 3e, and 3g, whereas the aliphatic thiols 3 a and 3 c yield a mixture of regioisomeric products 4 - 6. A higher selectivity with regard to the 17-oxo group was observed by using the thiol 3 b leading to 5 b. With the araliphatic thiol 31 compound 5f is selectively formed. In contrast to the described thioketal formation, the thiol 3d yields in addition to 4d a double Michael addition product 7, which was predominantly obtained by using other catalysts and/or a higher reaction temperature.
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页码:11 / 15
页数:5
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