SYNTHESIS OF GAMMA-LACTONES FROM INTERMEDIATE 2-(GAMMA-HYDROXYACYL)-IMIDAZOLES BY N-METHYLATION AND BASE-CATALYZED C-C BOND-CLEAVAGE - APPLICATION TO THE SYNTHESIS OF (+/-)-CAVERNOSINE

被引：12

作者：

DAVIES, DH ^{[1
]}

HAIRE, NA ^{[1
]}

HALL, J ^{[1
]}

SMITH, EH ^{[1
]}

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 37期

关键词：

D O I：

10.1016/S0040-4020(01)80461-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the allyl anions of 0-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of alpha- and gamma-attack. Greater steric hindrance in the anion (triisopropylsilyl VS t-butyldimethylsilyl) and in the aldehyde or ketone favours the gamma-products. Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to gamma-lactones. The method was applied to the synthesis of (+/-)-cavernosine.

引用

页码：7839 / 7856

页数：18

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