三取代Z烯烃合成中的脱羧Grob型碎片化反应：在海葵毒素A、盘状海绵醇和埃坡霉素D合成中的应用
Decarboxylative Grob-type fragmentations in the synthesis of trisubstituted Z olefins: application to peloruside A, discodermolide, and epothilone D.
作者信息
Prantz Kathrin, Mulzer Johann
机构信息
Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna, Austria.
出版信息
Angew Chem Int Ed Engl. 2009;48(27):5030-3. doi: 10.1002/anie.200901740.
Discriminating elimination: A new method for the synthesis of methyl-branched trisubstituted Z olefins, a structural motif in many polyketides with anticancer activity, relies on an (-)OH-induced decarboxylative Grob-type fragmentation (see scheme; Ms = mesyl). The starting materials are beta-mesyloxy lactones with a quaternary alpha center, which are prepared by aldol reactions in a diastereo- and enantioselective manner.
差别消除法
一种合成甲基支链三取代Z烯烃的新方法，这种结构基元存在于许多具有抗癌活性的聚酮化合物中，该方法依赖于（-）OH诱导的脱羧Grob型碎片化反应（见反应式；Ms = 甲磺酰基）。起始原料是具有季碳α中心的β-甲磺酰氧基内酯，它们通过醛醇缩合反应以非对映和对映选择性的方式制备。
Zotero 插件