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
收藏
页码：7409 / 7412
页数：4
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