文献类型：期刊文献

英文题名：Br?nsted acid catalyzed [4+2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities

作者：Hu, Teng[1];Zhao, Yuxuan[1];Luo, Xiaoyan[1];Li, Zhong[1];Yang, Wu-Lin[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, 130 Meilong Rd, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2024

卷号：22

期号：23

起止页码：4656

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20242316215726);WOS:【SCI-EXPANDED(收录号:WOS:001232559500001)，CCR-EXPANDED(收录号:WOS:001232559500001)】；

基金：This work is supported by the National Natural Science Foundation of China (22171081), Shanghai Rising-Star Program (23QA1402600) and Natural Science Foundation of Shanghai (23ZR1416700), Shanghai Agriculture Applied Technology Development Program (T2023309), and Fundamental Research Funds for the Central Universities (JKY01241718). The authors appreciate the Xiaoming Feng group at Shenzhen Bay Laboratory for a generous gift of the chiral N,N '-dioxide ligands. The authors also thank the Research Center of Analysis and Test of East China University of Science and Technology for the help with HRMS and NMR analyses.

语种：英文

摘要：The intermolecular [4 + 2] cycloaddition of o-hydroxy benzyl alcohols with isochroman ketals was realized by CF3CO2H catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45-98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)(3)/Feng's chiral N,N '-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good in vitro antifungal activities against Sclerotinia sclerotiorum and Rhizoctonia solani.