形式上的oxa-[3+3]环加成反应具有条件温和、可控性强，且可实现多步反应连续发生、多个化学键同时形成等优势，是合成具有多种生物活性的吡喃骨架结构化合物的有效方法,已成为新药研发的热点领域。本项目旨在系统研究“酚参与的形式oxa-[3+3]环加成反应”，发展更加温和、高效的构建苯并吡喃骨架结构的通用方法，并将其应用于天然产物bisabosqual 、 spirooliganone 、strongylin及类似物的的全合成中。同时，还将对合成的天然产物及类似物展开生物活性研究尤其是抗病毒活性以及构效关系的分析评价，为发现新颖的抗病毒药物及先导化合物奠定基础。目前，采用“酚参与的形式oxa-[3+3]环加成反应”策略完成了天然产物cannabicyclol、clusiacyclol A和B、eriobrucinol、iso-eriobrucinol A和B等的全合成，具有前期工作基础。

Developing novel synthetic methodology and applying it to the total synthesis of complex natural products is one of the most actively pursued fields in the synthetic organic community. The formal oxa-[3+3] cycloaddition reaction is among the most powerful methods in organic synthesis, as an attractive feature, is their ability to afford multiple bond simultaneous formations with regio and stereochemical control, and deliver the benzopyran products, are widely distributed stuctures in natural products and have shown many biological activities. This project focuses on the developing of new catalyst systems for the formal oxa-[3+3] cycloaddition of phenols with alph,beta-unsaturated aldehydes. Furthermore, we will apply the new synthetic methods and strategies to the synthesis of bisabosqual, spirooliganones, strongylin, and explore the common path toward these natural products and their analogs. Meanwhile, the biological activities of these compounds will be invstigated, intending to assay specifically for antivirus and SAR evaluation, the work of which will lay a foundation for discovering novel antivirus drug and lead compound. Most importantly, the success of this strategy in the total synthesies of cannabicyclol, clusiacyclol A and B, eriobrucinol, iso-eriobrucinol A and B have proved the validity and feasibility of our proposal.