Total Synthesis of Carbazole Alkaloid Murrayaquinone A

被引：4

作者：

Zhang, Kun ^{[1
]}

Xu, Hongjin ^{[1
]}

Liu, Zibo ^{[1
]}

Song, Chuanjun ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 39卷 / 04期

基金：

中国国家自然科学基金;

关键词：

murrayaquinone A; carbazole alkaloid; C-H alkenylation; total synthesis; PALLADIUM-CATALYZED SYNTHESIS; DERIVATIVES; PROGRESS;

D O I：

10.6023/cjoc201812005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Murrayaquinone A is a carbazolequinone alkaloid isolated from the root bark of Murraya euchrestifolia Hayata. It has been found to exhibit cardiotonic activity on heart muscle. Starting from the commercially available 3-acylindole, the total synthesis of Murrayaquinone A was realized in eight steps in an overall yield of 8%. The key step of our synthesis involves a palladium-catalyzed intramolecular alpha-C-H alkenylation of indole derivative to construct the carbazole A ring.

引用

页码：1142 / 1146

页数：5

共 49 条

[1] Palladium-Catalyzed Direct Arylation for the Synthesis of Indeno[2,1-b]pyrrol-8-ones [J].

Chang, Junbiao ;

Sun, Li ;

Dong, Jingjing ;

Shen, Zhenhua ;

Zhang, Yueteng ;

Wu, Jie ;

Wang, Ruiyong ;

Wang, Jinqian ;

Song, Chuanjun .

SYNLETT, 2012, (18) :2704-2706

[2] An Intramolecular Pyranone Diels-Alder Cycloaddition Approach to Cannabinol [J].

Fan, Fangfang ;

Dong, Jingjing ;

Wang, Jinqian ;

Song, Lina ;

Song, Chuanjun ;

Chang, Junbiao .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) :1337-1342

[3] Synthesis of an Advanced Intermediate of the Macrotricyclic Core of Roseophilin [J].

Hong, Meiling ;

Liu, Hui ;

Sun, Li ;

Jia, Feifei ;

Liu, Yuanyuan ;

Jiang, Qingwei ;

Song, Chuanjun ;

Chang, Junbiao .

SYNLETT, 2011, (20) :2995-2996

[4] Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823 [J].

Hoshino, Shotaro ;

Zhang, Lihan ;

Awakawa, Takayoshi ;

Wakimoto, Toshiyuki ;

Onaka, Hiroyasu ;

Abe, Ikuro .

JOURNAL OF ANTIBIOTICS, 2015, 68 (05) :342-344

[5] Divergent Syntheses of Carbazole Alkaloids [J].

Ji, Feixiang ;

Huang, He ;

Li, Mengyang ;

Guo, Yanqin ;

Song, Chuanjun ;

Chang, Junbiao .

SYNTHESIS-STUTTGART, 2018, 50 (19) :3921-3926

[6] Racemosins A and B, two novel bisindole alkaloids from the green alga Caulerpa racemosa [J].

Liu, Ding-Quan ;

Mao, Shui-Chun ;

Zhang, Hai-Yan ;

Yu, Xiao-Qing ;

Feng, Mei-Tang ;

Wang, Bin ;

Feng, Li-Hua ;

Guo, Yue-Wei .

FITOTERAPIA, 2013, 91 :15-20

[7] Recent Progress in Receptor Compounds Based on Carbazole Derivatives for Anion Recognition and Sensing [J].

Liu, Yong ;

Zhang, Feng ;

Zou, Linbo ;

Jian, Junyou ;

Bao, Xiaoping .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (12) :2485-2495

[8] Anionic [4+2] cycloaddition strategy in the regiospecific synthesis of carbazoles: formal synthesis of ellipticine and murrayaquinone A [J].

Mal, Dipakranjan ;

Senapati, Bidyut Kumar ;

Pahari, Pallab .

TETRAHEDRON, 2007, 63 (18) :3768-3781

[9] 3-Methoxy-2-methyl-carbazole-1,4-quinone, carbazomycins D and F from Streptomyces sp CMU-JT005 [J].

Ruanpanun, Pornthip ;

Dame, Zerihun Teklemariam ;

Laatsch, Hartmut ;

Lumyong, Saisamorn .

FEMS MICROBIOLOGY LETTERS, 2011, 322 (01) :77-81

[10] Enantioselective Fujiwara-Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)-NicOx Complexes [J].

Schiffner, Julia A. ;

Woeste, Thorsten H. ;

Oestreich, Martin .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (01) :174-182

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