Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids

Yanshi Wang; Fukai Xie; Bin Lin; Maosheng Cheng; Yongxiang Liu

doi:10.1002/chem.201800775

Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids

Chemistry. 2018 Sep 25;24(54):14302-14315. doi: 10.1002/chem.201800775. Epub 2018 Jul 6.

Authors

Yanshi Wang^{1

2}, Fukai Xie^{1

2

3}, Bin Lin^{1

2}, Maosheng Cheng^{1

2}, Yongxiang Liu^{1

2

3}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, P. R. China.
² Institute of Drug Research in Medicine Capital of China, Benxi, 117000, P. R. China.
³ Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, 110016, P. R. China.

PMID: 29624769
DOI: 10.1002/chem.201800775

Abstract

Indole alkaloids bearing the tetracyclic indoline scaffolds of 1H-pyrrolo[2,3-d]carbazole have shown fascinating chemical diversity and significant biological activities. The development of efficient synthetic methodologies for such a tetracyclic scaffold remains highly desirable in both synthetic chemistry and medicinal chemistry. This review outlines key strategies for the construction of the tetracyclic indoline scaffolds in total syntheses of many indole alkaloids. The key strategies include nucleophilic additions, Diels-Alder reactions, radical cyclizations, and palladium-catalyzed coupling reactions. The representative examples and their applications in the total syntheses are described here and discussed in depth.

Keywords: alkaloids; building blocks; cyclization; tetracyclic; total synthesis.

Publication types

Review