THE ENANTIOSELECTIVE SYNTHESIS OF THE POTENT DOPAMINE D1 AGONIST (1R,3S)-3-(1'-ADAMANTYL)-1-(AMINOMETHYL)-3,4-DIHYDRO-5,6-DIHYDROXY-1H-2-BENZOPYRAN (A77636)

被引：29

作者：

DENINNO, MP

PERNER, RJ

MORTON, HE

DIDOMENICO, S

机构：

[1] ABBOTT LABS,DEPT 47U,NEUROSCI RES,ABBOTT PK,IL 60064

[2] ABBOTT LABS,PHARMACEUT DISCOVERY,DEPT 45L,PROC RES,ABBOTT PK,IL 60064

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 26期

关键词：

D O I：

10.1021/jo00052a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.

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页码：7115 / 7118

页数：4

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