Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of δ-trialkylsilyloxy substituted ketones:: Total synthesis of (-)-centrolobine
Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of δ-trialkylsilyloxy substituted ketones:: Total synthesis of (-)-centrolobine
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DOI：
10.1021/ol035438t
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发表时间：
2003-10-16
期刊：
影响因子：
5.2
通讯作者：
Gharpure, SJ
中科院分区：
文献类型：
--
作者：
Evans, PA;Cui, J;Gharpure, SJ
δ-三烷基硅氧基取代酮与催化三溴化铋和三乙基硅烷的立体选择性分子内还原醚化反应为顺式-2，6-二取代四氢吡喃的构建提供了一种方便的方法。该方法在快速全合成抗生素（-）-centrolobine的关键步骤中得到了强调。
[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.