Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of δ-trialkylsilyloxy substituted ketones:: Total synthesis of (-)-centrolobine

被引：102

作者：

Evans, PA ^{[1
]}

Cui, J ^{[1
]}

Gharpure, SJ ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035438t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The stereoselective intramolecular reductive etherification of delta-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and triethylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetrahydropyrans. This method was highlighted in the key step of an expeditious total synthesis of the antibiotic, (-)-centrolobine.

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页码：3883 / 3885

页数：3

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