分子内氧化偶联反应在合成复杂吲哚生物碱骨架中的应用
收稿日期: 2013-01-15
修回日期: 2013-01-31
网络出版日期: 2013-02-01
基金资助
国家重点基础研究发展计划(973计划, No. 2010CB833200)资助项目.
Intramolecular Oxidative Coupling: Applications in Synthesis of Complex Indole Akaloid Scaffolds
Received date: 2013-01-15
Revised date: 2013-01-31
Online published: 2013-02-01
Supported by
Project supported by the National Basic Research Program of China (973 Program, No. 2010CB833200).
通过含有吲哚底物的分子内氧化偶联反应, 成功地构建了Communesin家族生物碱的螺吲哚啉季碳中心, 从而完成了(-)-Communesins A, B和F的对映选择性合成. 接下来我们发展了分子内氧化偶联/缩合串联反应策略, 得到了天然产物(-)-Vincorine的核心四环骨架, 然后再经过五步转化完成了Vincorine的全合成. 从药物化学角度来看, 分子内氧化偶联/缩合串联提供了一个快速方便地合成含有多环吲哚啉骨架的方法. 采用相同的串联反应策略, 我们分别从色胺衍生的β-酮酸酰胺和丙二酸二酰胺出发, 一步构建了多环螺吲哚啉和多环吲哚啉并吡咯环骨架分子.
谢卫青 , 左智伟 , 资伟伟 , 马大为 . 分子内氧化偶联反应在合成复杂吲哚生物碱骨架中的应用[J]. 有机化学, 2013 , 33(05) : 869 -876 . DOI: 10.6023/cjoc201301035
Intramolecular oxidative coupling of tryptamine incorporated amide was used to create the quaternary spiroindoline carbon center of communesins, which enabled a short asymmetric synthesis of (-)-communesins A and B and F. The fused tetra-ring framework of Vincorine was established by an intramolecular oxidative coupling/condensative cyclization process, which was further advanced to (-)-vincorine in 5 steps. From a medicinal standpoint, such a cascade process provides a highly diverse, efficient method for the construction of polycyclic spiroindoline scaffolds. Starting from easily accessible tryptamine incorporated β-ketoamides and malonamides, polyclic spiroindolines and pyrroloindolines could be directly obtained by adopting the same cascade strategy.
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