Intramolecular Oxidative Coupling: Applications in Synthesis of Complex Indole Akaloid Scaffolds

doi:10.6023/cjoc201301035

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 869-876.DOI: 10.6023/cjoc201301035 Previous Articles Next Articles

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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

谢卫青, 左智伟, 资伟伟, 马大为

中国科学院上海有机化学研究所生命有机化学国家重点实验室上海 200032

收稿日期:2013-01-15 修回日期:2013-01-31 发布日期:2013-02-01
通讯作者: 谢卫青,xiewq@sioc.ac.cn;马大为,madw@sioc.ac.cn E-mail:xiewq@sioc.ac.cn;madw@sioc.ac.cn
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

Xie Weiqing, Zuo Zhiwei, Zi Weiwei, Ma Dawei

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032

Received:2013-01-15 Revised:2013-01-31 Published:2013-02-01
Supported by:
Project supported by the National Basic Research Program of China (973 Program, No. 2010CB833200).

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.

Key words: intramolecular oxidative coupling, indole alkaloids, total synthesis, polycyclic spiroindoline, pyrroloindoline

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Xie Weiqing, Zuo Zhiwei, Zi Weiwei, Ma Dawei. Intramolecular Oxidative Coupling: Applications in Synthesis of Complex Indole Akaloid Scaffolds[J]. Chin. J. Org. Chem., 2013, 33(05): 869-876.

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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

Intramolecular Oxidative Coupling: Applications in Synthesis of Complex Indole Akaloid Scaffolds

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