Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids
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 c...
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| Published in | Chemistry : a European journal Vol. 24; no. 54; pp. 14302 - 14315 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Wiley Subscription Services, Inc
25.09.2018
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| 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.
Tetracyclic indolines have acted as versatile building blocks for the syntheses of diverse indole alkaloids through half a century. There is a wide range of synthetic strategies for the common frameworks, which could be classified into nucleophilic additions, Diels–Alder reactions, radical cyclizations, palladium‐catalyzed coupling reactions, etc. The representative examples and their applications in the total syntheses are described here and discussed in depth. |
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| AbstractList | Indole alkaloids bearing the tetracyclic indoline scaffolds of 1
H
‐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. 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.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. 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, palladium-catalyzed coupling reactions, etc. The representative examples and their applications in the total syntheses are described here and discussed in depth. 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. 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. Tetracyclic indolines have acted as versatile building blocks for the syntheses of diverse indole alkaloids through half a century. There is a wide range of synthetic strategies for the common frameworks, which could be classified into nucleophilic additions, Diels–Alder reactions, radical cyclizations, palladium‐catalyzed coupling reactions, etc. The representative examples and their applications in the total syntheses are described here and discussed in depth. |
| Author | Xie, Fukai Liu, Yongxiang Lin, Bin Wang, Yanshi Cheng, Maosheng |
| Author_xml | – sequence: 1 givenname: Yanshi surname: Wang fullname: Wang, Yanshi organization: Institute of Drug Research in Medicine Capital of China – sequence: 2 givenname: Fukai surname: Xie fullname: Xie, Fukai organization: Shenyang Pharmaceutical University – sequence: 3 givenname: Bin surname: Lin fullname: Lin, Bin email: randybinlin@gmail.com organization: Institute of Drug Research in Medicine Capital of China – sequence: 4 givenname: Maosheng surname: Cheng fullname: Cheng, Maosheng email: mscheng@syphu.edu.cn organization: Institute of Drug Research in Medicine Capital of China – sequence: 5 givenname: Yongxiang orcidid: 0000-0003-0364-0137 surname: Liu fullname: Liu, Yongxiang email: yongxiang.liu@syphu.edu.cn organization: Shenyang Pharmaceutical University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29624769$$D View this record in MEDLINE/PubMed |
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| Keywords | building blocks total synthesis cyclization tetracyclic alkaloids |
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| Snippet | Indole alkaloids bearing the tetracyclic indoline scaffolds of 1H‐pyrrolo[2,3‐d]carbazole have shown fascinating chemical diversity and significant biological... Indole alkaloids bearing the tetracyclic indoline scaffolds of 1 H ‐pyrrolo[2,3‐ d ]carbazole have shown fascinating chemical diversity and significant... Indole alkaloids bearing the tetracyclic indoline scaffolds of 1H-pyrrolo[2,3-d]carbazole have shown fascinating chemical diversity and significant biological... |
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| SubjectTerms | Alkaloids Biodiversity building blocks Carbazole Carbazoles Chemical reactions Chemistry Construction cyclization Heterocyclic compounds Indoles Organic chemistry Palladium Scaffolds tetracyclic total synthesis |
| Title | Synthetic Approaches to Tetracyclic Indolines as Versatile Building Blocks of Diverse Indole Alkaloids |
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