SYNTHESIS OF THE 4 STEREOISOMERS OF 4-AMINOADAMANTANE-2-CARBOXYLIC ACID, RIGID ANALOGS OF GAMMA-AMINOBUTYRIC ACID

被引:6
作者
BLACK, RM
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1982年 / 01期
关键词
D O I
10.1039/p19820000073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic routes to the 4 stereoisomers of 4-aminoadamantane-2-carboxylic acid are described. .pi.-Route cyclizations to 2,4-disubstituted adamantanes are expanded to obtain 4eq- and 4az-acetamidoadamantan-2-ones. These are converted into acetamido-nitriles using tosylmethyl isocyanide and subsequently hydrolyzed to 3 of the amino-acids. The diaxial isomer is prepared by a stereospecific nitrene insertion reaction. Mass spectra of the amino-acids and their ethyl esters are reported. [Biological activity of the compounds is described.].
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页码:73 / 77
页数:5
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