SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .26. HYDRIDE REDUCTION OF ERYTHRINAN-7,8-DIONES AND 7-O-METHANESULFONYL-8-OXO-ERYTHRINANS

被引：0

作者：

TSUDA, Y ^{[1
]}

SAKAI, Y ^{[1
]}

AKIYAMA, K ^{[1
]}

ISOBE, K ^{[1
]}

机构：

[1] SHOWA COLL PHARMACEUT SCI, MACHIDA, TOKYO 194, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1991年 / 39卷 / 08期

关键词：

ERYTHRINAN-7,8-DIONE; HYDRIDE REDUCTION; SODIUM BOROHYDRIDE; SOLVENT EFFECT; STEREOCHEMISTRY; EPIMERIZATION; 7-O-METHANESULFONYL-8-OXOERYTHRINAN; LITHIUM ALUMINUM HYDRIDE;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The stereochemistry of hydride reduction of erythrinan-7,8-diones was markedly affected by the bulkiness of the reagent and the polarity of the solvent: sodium borohydride in ethanol-tetrahydrofuran gave the 7-beta-hydroxy isomers and tetrabutylammonium borohydride in methanol gave the 7-alpha-hydroxy isomers, stereoselectively. This can be explained in terms of fluctuation of the balance between product development control and approach control. The structures of the products were established by chemical and spectroscopic means. Their O-mesylates were hydrolyzed under basic conditions with epimerization to give a mixture of alcohols with a preference for the 7-beta-hydroxy derivatives. A similar epimerization of the mesyloxy group was also observed in lithium aluminum hydride reduction.

引用

页码：2120 / 2123

页数：4