Affiliation:
1. College of Pharmacy Pusan National University Busan 46241 Republic of Korea
2. New Drug Development Center Daegu-Gyeongbuk Medical Innovation Foundation Daegu 41061 Republic of Korea
3. Research Institute for Drug Development Pusan National University Busan 46241 Republic of Korea
Abstract
AbstractSynthesis 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.