Formation of γ-lactones through CAN-mediated oxidative cleavage of hemiketals

被引：14

作者：

Jacobine, Alexander M. ^{[1
]}

Lin, Weimin ^{[1
]}

Walls, Bethany ^{[1
]}

Zercher, Charles K. ^{[1
]}

机构：

[1] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 18期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/jo801258h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The generation of substituted gamma-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an alpha-heteroatom. Formation of the gamma-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.

引用

页码：7409 / 7412

页数：4

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