Unusual oxidation reactions of 7 alpha-methyl- and 7 alpha-phenylcholest-5-ene-3 beta,7 beta-diol

被引：0
|
作者：
Morzycki, JW
Dabrowski, Z
Trusewicz, M
Wilczewska, AZ
机构：
[1] Institute of Chemistry, University of Warsaw, Bialystok Branch
来源：
MONATSHEFTE FUR CHEMIE | 1996年 / 127卷 / 12期
关键词：
steroids; ozonization; CrO3; oxidation; epoxidation; B-seco steroids;
D O I：
10.1007/BF00807796
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Ozonation of 7 alpha-methyl(or 7 alpha-phenyl) cholest-5-ene-3 beta,7 beta-diol 3-TBDMS ether afforded the corresponding 5 beta,6 beta-epoxy derivatives. The same product was formed by MCPBA oxidation. The reaction of 7 alpha-phenylcholest-5-ene- 3 beta,7 beta-diol with CrO3 yielded 3,7-dioxo-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B-seco aldehyde was obtained from 7 alpha-methylcholest-5-ene-3 beta,7 beta-diol in addition to 7-methylcholesta-4,6-dien-3-one. Jones oxidation of 7 alpha-phenylcholest-5-ene-3 3 beta,7 beta-diol or B-seco-aldehyde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated as its methyl ester upon treatment with diazomethane.
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页码：1283 / 1289
页数：7
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