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The Synthesis of Substituted α, β-Butenolides from γ-Hydroxy-α, β-Acetylenic Esters

 

作者: Drury Caine,   TroyL. Smith,  

 

期刊: Synthetic Communications  (Taylor Available online 1980)
卷期: Volume 10, issue 10  

页码: 751-759

 

ISSN:0039-7911

 

年代: 1980

 

DOI:10.1080/00397918008061839

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The α, β-butenolide ring system is found in a number of physiologically important natural products2and there has been recent interest in the development of methods of synthesis of compounds of this type.3It is well known that α, β-unsubstituted butenolides may be prepared by catalytic hydrogenation of γ-hydroxy acetylenic acids.4,5bRecently, an excellent route of γ-hydroxy acetylenic esters which involves the addition of the lithium acetylide salts of propiolic esters to aldehydes5and ketones6has become available. We have carried out the addition of ethyl lithiopropiolate (1) to cyclohexanone (2) and 4-t-butylcyclohexanone (3) and wish to report the conversion of these adducts into corresponding β-methyl or β-methyl-α-allyl-α, β-butenolides.

 

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