Synthesis of Benzo[a]fluorene, Benzo[c]fluorene, and Benzo[j]fluoranthene via a Lewis Acid‐Catalyzed Prins‐Type Cycloaromatization: Application to the Total Synthesis of Viridistratin A
Synthesis of benzo[a]fluorene, benzo[c]fluorene, and benzo[j]fluoranthene have been accomplished from readily accessible enol ether precursors via a Lewis acid‐catalyzed Prins‐type cycloaromatization. Mechanistically, it was proposed that Lewis acids catalyze the generation of oxonium species, which...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2024-02, Vol.366 (3), p.390-395 |
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| container_issue | 3 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 366 |
| creator | Jeong, Myeonggyo Yoon, Moonsang Nguyen, Long Huu Kim, Soyeong Han, Jinhee Tran, Cong So Kim, Jisu Jo, Jeyun Jung, Young‐Suk Yoo, Jin‐Wook Yun, Hwayoung |
| description | Synthesis of benzo[a]fluorene, benzo[c]fluorene, and benzo[j]fluoranthene have been accomplished from readily accessible enol ether precursors via a Lewis acid‐catalyzed Prins‐type cycloaromatization. Mechanistically, it was proposed that Lewis acids catalyze the generation of oxonium species, which accelerate subsequent annulation and aromatization. This protocol offers the benefit of an operationally simple, transition‐metal‐free, and air‐tolerant reaction condition, enabling gram‐scale syntheses of the desired products. The total synthesis of viridistratin A further supported this synthetic strategy for establishing polycyclic aromatic hydrocarbon architectures. |
| doi_str_mv | 10.1002/adsc.202300600 |
| format | Article |
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| ispartof | Advanced synthesis & catalysis, 2024-02, Vol.366 (3), p.390-395 |
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| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Cycloaromatization Enol ether Non-alternant PAH Total synthesis Viridistratin |
| title | Synthesis of Benzo[a]fluorene, Benzo[c]fluorene, and Benzo[j]fluoranthene via a Lewis Acid‐Catalyzed Prins‐Type Cycloaromatization: Application to the Total Synthesis of Viridistratin A |
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