A hetero-Diels-Alder approach to complex pyrones: An improved synthesis of the spongistatin AB spiroketal

被引：23

作者：

Crimmins, MT ^{[1
]}

Smith, AC ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol0601601

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.

引用

页码：1003 / 1006

页数：4

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