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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