Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans

doi:10.6023/cjoc201204029

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2040-2053.DOI: 10.6023/cjoc201204029 Previous Articles Next Articles

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芳基氧化偶联试剂在天然活性成分联苯并环辛烯类木脂素合成中的应用进展

刘延泽^a, 常俊标^b, 谢晶曦^c

a 中国医学科学院协和医学院药用植物研究所北京 100193;
b 郑州大学化学系郑州 450000;
c 中国医学科学院协和医学院药物研究所北京 100050

收稿日期:2012-04-26 修回日期:2012-06-14 发布日期:2012-06-21
通讯作者: 刘延泽 E-mail:yzliu@implad.ac.cn
基金资助:
科技部国际科技合作(No. 2007DFB31610)资助项目.

Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans

Liu Yanze^a, Chang Junbiao^b, Xie Jingxi^c

a Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193;
b Department of Chemistry, Zhengzhou University, Zhengzhou 450000;
c Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100050

Received:2012-04-26 Revised:2012-06-14 Published:2012-06-21
Supported by:
Project supported by the International Cooperation Program of the Ministry of Science and Technology of China (No. 2007DFB31610).

Dibenzocyclooctadiene lignans, such as schizandrin, gomisin are a kind of important natural product with significant biological activities, especially for liver disease. Several total synthetic strategies had been investigated and succeed in the application of oxidative coupling reagents including intramolecular and intermolecular coupling such as TlTFA, RuTFA, Fe(ClO₄)₃, MoCl₅, and PhI(OAc)₂ etc. These applications of various aryl-aryl oxidative coupling reagents for the synthesis of dibenzocyclooctadiene lignans published in recent 20 years are reviewed, together with author’s experience in this area. Finally, the new synthetic hypothesis through the connection between biphenyl aryl piece and aliphatic piece is proposed.

Key words: dibenzocyclooctadiene, lignans, aryl-aryl oxidative coupling, natural product, Schisandraceae, total synthesis

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Liu Yanze, Chang Junbiao, Xie Jingxi. Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans[J]. Chin. J. Org. Chem., 2012, 32(11): 2040-2053.

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芳基氧化偶联试剂在天然活性成分联苯并环辛烯类木脂素合成中的应用进展

Progress of Aryl-aryl Oxidative Coupling Reagents in the Synthetic Chemistry of Dibenzocyclooctadiene Lignans

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