4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

被引：13
|
作者：
Burns, Michael J. [1 ]
Ronson, Thomas O. [1 ]
Taylor, Richard J. K. [1 ]
Fairlamb, Ian J. S. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
基金：
英国工程与自然科学研究理事会;
关键词：
heterocycles; Mitsunobu reaction; oxa-Michael addition; 2-pyrone; vinyl ethers; TRIACETIC ACID LACTONE; PYRONES; 4-HYDROXY-6-METHYL-2-PYRONE; ALKYLATION; 2-PYRONES; ALPHA;
D O I：
10.3762/bjoc.10.116
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.
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页码：1159 / 1165
页数：7
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