四纤维丝菌素C1 - C20及C21 - C40片段的合成
Synthesis of C1-C20 and C21-C40 fragments of tetrafibricin.
作者信息
Gudipati Venugopal, Curran Dennis P
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA.
出版信息
Tetrahedron Lett. 2011 Apr 27;52(17):2254-2257. doi: 10.1016/j.tetlet.2011.01.086.
Abstract
Efficient syntheses of suitably functionalized top and bottom fragments of tetrafibricin are described. The bottom fragment is prepared by two consecutive Kocienski-Julia couplings, while the top fragment synthesis features a dithiane alkylation and a Horner-Wadsworth-Emmons reaction.
摘要
本文描述了对纤维四糖素的顶部和底部片段进行适当官能化的高效合成方法。底部片段通过两个连续的科钦斯基-朱利亚偶联反应制备，而顶部片段的合成则以二硫烷烷基化反应和霍纳-沃兹沃思-埃蒙斯反应为特征。
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3
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