Photoredox-Catalyzed Cascade Reactions Involving Aryl Radical: Total Synthesis of (±)-Norascyronone A and (±)-Eudesmol

Herein, we have developed two types of photoredox-catalyzed cascade reactions using diaryliodonium salts for the concise synthesis of norascyronone A and β-eudesmol. A rationally designed photoredox-catalyzed arylation/cyclization/Friedel–Crafts cascade reaction of enone was exploited to generate th...

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Bibliographic Details
Published in:Organic letters 2021-12, Vol.23 (23), p.9073-9077
Main Authors: Xu, Ze-Jun, Liu, Xu-Yuan, Zhu, Ming-Zhu, Xu, Yu-Liang, Yu, Yue, Xu, Hai-Ruo, Cheng, Ai-Xia, Lou, Hong-Xiang
Format: Article
Language:English
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Summary:Herein, we have developed two types of photoredox-catalyzed cascade reactions using diaryliodonium salts for the concise synthesis of norascyronone A and β-eudesmol. A rationally designed photoredox-catalyzed arylation/cyclization/Friedel–Crafts cascade reaction of enone was exploited to generate the norascyronone polycyclic skeleton. A visible-light-induced radical cyclization/acyloxy-migration reaction was explored to forge the decalin skeleton of eudesmol, and mechanistic studies indicated the reaction was initiated by one-electron oxidation of the enol ester.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03319