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

被引：86

作者：

Wang, Yanshi ^{[1
,2
]}

Xie, Fukai ^{[1
,2
,3
]}

Lin, Bin ^{[1
,2
]}

Cheng, Maosheng ^{[1
,2
]}

Liu, Yongxiang ^{[1
,2
,3
]}

机构：

[1] Shenyang Pharmaceut Univ, Minist Educ, Key Lab Struct Based Drug Design & Discovery, Shenyang 110016, Liaoning, Peoples R China

[2] Inst Drug Res Med Capital China, Benxi 117000, Peoples R China

[3] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Liaoning, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 54期

关键词：

alkaloids; building blocks; cyclization; tetracyclic; total synthesis; ASPIDOSPERMATAN-TYPE ALKALOIDS; ASYMMETRIC TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; NONREARRANGED MONOTERPENOID UNIT; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CHLOROQUINE-POTENTIATING ACTION; TANDEM RADICAL CYCLIZATIONS; INTRAMOLECULAR DIELS-ALDER; CONCISE TOTAL-SYNTHESIS; NATURAL-PRODUCTS;

D O I：

10.1002/chem.201800775

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：14302 / 14315

页数：14

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