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
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
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DOI：
10.1016/s0040-4020(01)80461-0
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发表时间：
1992-09-11
期刊：
影响因子：
2.1
通讯作者：
SMITH, EH
中科院分区：
文献类型：
--
作者：
DAVIES, DH;HAIRE, NA;SMITH, EH
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.
