Selective bromination of dihydroquinopimaric acid

被引：0
|
作者：
I. E. Smirnova
O. B. Kazakova
E. V. Tret’yakova
A. N. Lobov
L. V. Spirikhin
G. A. Tolstikov
K. Yu. Suponitskii
机构：
[1] Russian Academy of Sciences,Institute of Organic Chemistry, Ufa Research Center
[2] Russian Academy of Sciences,Nesmeyanov Institute of Organometallic Compounds
来源：
Russian Journal of Organic Chemistry | 2011年 / 47卷
关键词：
Bromine; Acid Methyl Ester; Bromine Atom; Polymorphic Modification; Electrophilic Addition;
D O I：
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学科分类号：
摘要：
The reaction of dihydroquinopimaric acid methyl ester with bromine was found to be chemo- and stereoselective. Regardless of the solvent (acetic acid, methanol, dioxane), bromination of the title compound with an equimolar amount of bromine occurs as electrophilic addition at the double C19=C20 bond with formation of 14α-hydroxy- or 14α-methoxy-19R-bromo derivatives. The reaction with excess bromine (3 equiv) leads to the formation of 16S-bromo derivatives. The bromination process is accompanied by formation of epoxy bridge between the C14 and C20 atoms. X-Ray analysis revealed two polymorphic modifications of (16S,19R)-16,19-dibromo-14β,20-epoxydihydroquinopimaric acid methyl ester.
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页码：1385 / 1389
页数：4
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