Facile construction of diverse polyheterocyclic scaffolds via gold-catalysed dearomative spirocyclization/1,6-addition cascade

被引：27

作者：

He, Yi ^{[1
]}

Wu, Danjun ^{[2
]}

Li, Zhenghua ^{[1
]}

Robeyns, Koen ^{[3
]}

Van Meervelt, Luc ^{[4
]}

Van der Eycken, Erik V. ^{[1
,5
]}

机构：

[1] Katholieke Univ Leuven, Dept Chem, LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, 18 Chaowang Rd, Hangzhou 310014, Zhejiang, Peoples R China

[3] Catholic Univ Louvain, Inst Condensed Matter & Nanosci IMCN, 1 Pl Louis Pasteur, B-1348 Louvain La Neuve, Belgium

[4] Katholieke Univ Leuven, Dept Chem, Biomol Architecture, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[5] RUDN Univ, Peoples Friendship Univ Russia, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 25期

关键词：

MASKED O-BENZOQUINONES; ASYMMETRIC DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; MULTICOMPONENT REACTIONS; MOLECULAR DIVERSITY; RECENT PROGRESS; DIELS-ALDER; CYCLIZATION; DESIGN; TRANSFORMATIONS;

D O I：

10.1039/c9ob01299k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A gold-catalysed post-Ugi chemo- and diastereoselective cascade dearomative spirocyclization/1,6-addition sequence is disclosed for the synthesis of diverse fused polyheterocyclic scaffolds bearing indole, pyrrole, benzothiophene, furan or electron-rich arene moieties from easily available building blocks. The effectiveness and efficiency of this diversity-oriented approach has been proved in the rapid construction of 28 fused polyheterocyclic scaffolds with a good building-block variability and structural complexity in two operational steps.

引用

页码：6284 / 6292

页数：9

共 73 条

[61] Asymmetric dearomatization of phenols [J].

Sun, Wangsheng ;

Li, Guofeng ;

Hong, Liang ;

Wang, Rui .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (07) :2164-2176

[62] Natural product-like synthetic libraries [J].

Thomas, Gemma L. ;

Johannes, Charles W. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2011, 15 (04) :516-522

[63]

Trabocchi A., 2013, Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology

[64]

UGI I, 1959, ANGEW CHEM INT EDIT, V71, P386

[65] Gold-Catalyzed Intramolecular Dearomatization of Phenols with Allenoates for the Synthesis of Spirocyclohexadienones [J].

Wang, Hongyu ;

Wang, Kaiye ;

Xiang, Yanan ;

Jiang, Han ;

Wan, Xiuyan ;

Li, Na ;

Tang, Bo .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) :2352-2357

[66] Development of Catalysts and Ligands for Enantioselective Gold Catalysis [J].

Wang, Yi-Ming ;

Lackner, Aaron D. ;

Toste, F. Dean .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) :889-901

[67] Stable gold(III) catalysts by oxidative addition of a carbon-carbon bond [J].

Wu, Chung-Yeh ;

Horibe, Takahiro ;

Jacobsen, Christian Borch ;

Toste, F. Dean .

NATURE, 2015, 517 (7535) :449-454

[68] Recent Progress on Gold-catalyzed Dearomatization Reactions [J].

Wu Wen-Ting ;

Zhang Liming ;

You Shu-Li .

ACTA CHIMICA SINICA, 2017, 75 (05) :419-438

[69] Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols [J].

Wu, Wen-Ting ;

Xu, Ren-Qi ;

Zhang, Liming ;

You, Shu-Li .

CHEMICAL SCIENCE, 2016, 7 (05) :3427-3431

[70] Catalytic asymmetric dearomatization (CADA) reactions of phenol and aniline derivatives [J].

Wu, Wen-Ting ;

Zhang, Liming ;

You, Shu-Li .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (06) :1570-1580

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