|
|||||
|
|
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 |
|
| Authors: | Myeonggyo Jeong Moonsang Yoon Long Huu Nguyen Soyeong Kim Jinhee Han Cong So Tran Jisu Kim Jeyun Jo Young-Suk Jung Jin-Wook Yoo Hwayoung Yun |
| Affiliation: | 1. College of Pharmacy, Pusan National University, Busan, 46241 Republic of Korea These authors contributed equally;2. College of Pharmacy, Pusan National University, Busan, 46241 Republic of Korea New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu, 41061 Republic of Korea;3. College of Pharmacy, Pusan National University, Busan, 46241 Republic of Korea;4. College of Pharmacy, Pusan National University, Busan, 46241 Republic of Korea Research Institute for Drug Development, Pusan National University, Busan, 46241 Republic of Korea |
| Abstract: | 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. |
| Keywords: | Cycloaromatization Enol ether Non-alternant PAH Total synthesis Viridistratin |