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烯烃闭环复分解反应(RCM)在生物活性重要生物碱、萜类化合物、聚酮化合物及其他次生代谢产物合成中的近期应用。

Recent applications of olefin ring-closing metathesis (RCM) in the synthesis of biologically important alkaloids, terpenoids, polyketides and other secondary metabolites.

作者信息

Gaich Tanja, Mulzer Johann

机构信息

Institut für Organische Chemie der Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria.

出版信息

Curr Top Med Chem. 2005;5(15):1473-94. doi: 10.2174/156802605775009793.

Abstract

With the commercial availability of well-defined ruthenium metathesis catalysts which combine high stability and broad functional group compatibility with undiminished activity, ring-closing metathesis (RCM) is now routinely integrated in the planning of natural product syntheses. Thus, ring sizes of practically any kind from five onward may be formed. The presence of heteroatoms such as oxygen and nitrogen is of minor importance. Ring-strain and the presence of additional double bonds may be overcome by judicious selection of conditions. A major drawback of macrocyclic RCM still is the lack of E/Z stereocontrol. Nevertheless, the current overview will demonstrate the overwhelming power and scope of RCM in the total synthesis of structurally demanding natural products.

摘要

随着具有高稳定性、广泛官能团兼容性且活性不减的明确钌复分解催化剂的商业可得,关环复分解反应(RCM)如今在天然产物合成规划中已常规应用。因此,实际上从五元起的任何种类的环大小都可以形成。氧和氮等杂原子的存在影响较小。通过明智地选择条件,可以克服环张力和额外双键的存在。大环RCM的一个主要缺点仍然是缺乏E/Z立体控制。尽管如此,当前的综述将展示RCM在结构复杂的天然产物全合成中的巨大威力和应用范围。

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