Selective total synthesis of callipeltoside A: two approaches to the macrolactone fragment
Selective total synthesis of callipeltoside A: two approaches to the macrolactone fragment
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DOI：
10.1016/j.tet.2008.02.001
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发表时间：
2008-05-19
期刊：
影响因子：
2.1
通讯作者：
Jaeschke, Georg
中科院分区：
文献类型：
--
作者：
Evans, David A.;Burch, Jason D.;Jaeschke, Georg
本文报道了三七皂苷A的不对称全合成方法。包括两种大内酯亚基的合成：第一种是依靠爱尔兰-克莱森重排生成三取代烯烃几何构型，第二种是利用不对称的乙烯基羟醛反应。还公开了糖和氯环丙烷侧链片段的对映选择性合成。该天然产物的相对和绝对立体化学由片断与侧链片断的两个对映体偶联而确定。(C)2008爱思唯尔有限公司。保留所有权利。
The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment. (C) 2008 Elsevier Ltd. All rights reserved.