Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 15, Pages 2479-2501Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200473
Keywords
Aspidosperma alkaloids; Kopsia alkaloids; Total synthesis; Tetracyclic pyridocarbazoles; All-carbon quaternary centers
Categories
Funding
- National Natural Science Foundation of China [81803383]
- 111 Project [D20015]
- Hubei Provincial Natural Science Foundation of China [2020CFB205]
- Educational Commission of Hubei Province of China [Q20201204]
- Start-up Funding for High-Level Talents of China Three Gorges University [8220309]
- Natural Science Foundation of Zhejiang Province of China [LQ21B020006]
Ask authors/readers for more resources
This review discusses the synthesis of tetracyclic pyridocarbazoles, focusing on different approaches for establishing the all-carbon quaternary center at C5. Classic synthetic reactions, palladium-catalyzed asymmetric decarboxylative allylation reactions, and thiourea-catalyzed asymmetric Michael addition reactions have been employed. Late-stage key transformations in the total syntheses of aspidosperma and kopsia alkaloids are also described.
Over the past decades, aspidosperma and kopsia alkaloids have attracted significant interest by the organic synthetic community owing to their intricate fused-ring structures and broad biological activities. Consequently, numerous strategically distinct total syntheses have been accomplished, among which tetracyclic pyridocarbazoles have seen widespread adoption as versatile building blocks. In this review, we elaborate and discuss the synthesis of such tetracyclic pyridocarbazoles according to the different approaches for the establishment of the all-carbon quaternary center at C5. This includes (1) classic synthetic reactions (cycloaddition, Michael addition, nucleophilic substitution, and Claisen rearrangement), (2) palladium-catalyzed asymmetric decarboxylative allylation reactions, and (3) thiourea-catalyzed asymmetric Michael addition reactions. Furthermore, we also describe the late-stage key transformations in the realm of the total syntheses of aspidosperma and kopsia alkaloids.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available