A Maitland-Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones

被引：11
|
作者：
Clarke, Paul A. [1 ]
Sellars, Philip B. [1 ]
Nasir, Nadiah Mad [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 16期
关键词：
DIELS-ALDER REACTIONS; MARINE SPONGE; ABSOLUTE-CONFIGURATION; LASONOLIDE-A; PHORBAS SP; PHORBOXAZOLES; POT; CYCLOADDITION; CONSTRUCTION; MACROLIDE;
D O I：
10.1039/c5ob00292c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Maitland-Japp reaction has been extended to the synthesis of highly functionalised dihydropyran-4-ones. These dihydropyran-4-ones can in turn be converted stereoselectively into tetrahydropyran-4-ones with tertiary and quaternary stereocentres via the one-pot addition of hydride or carbon nucleophiles and trapping with carbon electrophiles. The utility of this method is demonstrated by providing access to the functionalised tetrahydropyran units present in a component of the Civet fragrance and the anticancer polyketide lasonolide A.
引用
收藏
页码：4743 / 4750
页数：8
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