Asymmetric Synthesis of (+)-Polyanthellin A

被引：85

作者：

Campbell, Matthew J. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 30期

基金：

美国国家科学基金会;

关键词：

INTRAMOLECULAR CYCLOPROPANATION; GENERAL STRATEGY; SCLEROPHYTIN-A; DITERPENES; ALDEHYDES; TETRAHYDROFURANS; CYCLOADDITIONS; ALPHA;

D O I：

10.1021/ja904136q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise and convergent route to (+)-polyanthellin A is presented. This synthesis features a diastereoselective cyclopropane/aldehyde [3+2] cycloaddition to install the hydroisobenzofuran core. The use of MADNTf(2) as a potent, bulky Lewis acid was essential to allow a labile B-silyloxy aldehyde to be used in the cycloaddition. Other key steps include a ring-closing metathesis and a selective olefin oxidation

引用

页码：10370 / +

页数：3

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