An intramolecular Diels-Alder strategy for the asbestinins: Enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12

被引：33

作者：

Crimmins, Michael T. ^{[1
]}

Ellis, J. Michael ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 05期

关键词：

D O I：

10.1021/jo0712695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Graphics] The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

引用

页码：1649 / 1660

页数：12

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