THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .18. THE OXIDATION OF PROGESTERONE UNDER GOAGGIII CONDITIONS

被引：5
|
作者：
BARTON, DHR
DOLLER, D
机构：
来源：
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1991年 / 56卷 / 05期
关键词：
D O I：
10.1135/cccc19910984
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The oxidation of pregn-4-ene-3,20-dione (progesterone) by the GoAgg(III) system (aqueous hydrogen peroxide, ferric chloride, picolinic acid in pyridine-acetic acid solution) has been investigated. Two tri-keto derivatives were isolated and identified as pregn-4-ene-3,6,20-trione and pregn-4-ene-3,12,20-trione. The third major product isolated was identified as the unstable 5-alpha-formyl-A-nor-pregnane-3,20-dione, which deformylated spontaneously to A-nor-5-beta-pregnane-3,20-dione. A mechanism for the A-ring contraction is proposed, based upon the participation of a carbon-Fe(V) intermediate.
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页码：984 / 990
页数：7
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