Synthesis of Functionalized 4‑Hydroxy Carbazoles and Carbazole Alkaloids via Ring Expansion of Indole Cyclopentanone

The exploration of a ring expansion reaction from indole cyclopentanone to generate a range of diversely functionalized 4-hydroxyl carbazole frameworks, representing the core structure of numerous carbazole alkaloids, has been conducted under mild reaction conditions. This approach exhibits broad fu...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-06, Vol.89 (12), p.8845-8850
Main Authors: Pan, Xiaolong, Dong, Boyang, Wu, Yangang, Gao, Beiling, Song, Chuanjun
Format: Article
Language:English
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Summary:The exploration of a ring expansion reaction from indole cyclopentanone to generate a range of diversely functionalized 4-hydroxyl carbazole frameworks, representing the core structure of numerous carbazole alkaloids, has been conducted under mild reaction conditions. This approach exhibits broad functional group tolerance and moderate to good yields. The practical applicability of this strategy has been demonstrated through the concise syntheses of carbazomycins A, D, and G.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00730