通过δ-三烷基硅氧基取代的酮的还原醚化反应立体选择性构建顺式-2,6-二取代四氢吡喃：（-）-中心洛宾的全合成。
Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of delta-trialkylsilyloxy substituted ketones: total synthesis of (-)-centrolobine.
作者信息
Evans P Andrew, Cui Jian, Gharpure Santosh J
机构信息
Department of Chemistry, 800 East Kirkwood Avenue, Indiana University, Bloomington, Indiana 47405, USA.
出版信息
Org Lett. 2003 Oct 16;5(21):3883-5. doi: 10.1021/ol035438t.
Abstract
[reaction: see text] 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.
摘要
[反应：见正文] 用催化量的三溴化铋和三乙基硅烷对δ-三烷基硅氧基取代的酮进行立体选择性分子内还原醚化反应，为构建顺式-2,6-二取代四氢吡喃提供了一种简便方法。该方法在抗生素（-）-百部碱的快速全合成关键步骤中得到了突出体现。
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