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

页码：4743 / 4750

页数：8

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