Total Syntheses of (鈭?-Spirooliganones A and B and Their Diastereoisomers: Absolute Stereochemistry and Inhibitory Activity against Coxsackie Virus B3

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• 作者：Nan Zhao ; Xiaodong Ren ; Jinhong Ren ; Haining L眉 ; Shuanggang Ma ; Rongmei Gao ; Yuhuan Li ; Song Xu ; Li Li ; Shishan Yu
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：17
• 期：12
• 页码：3118-3121
• 全文大小：375K
• ISSN：1523-7052

文摘

To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (1鈥?b>8) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels鈥揂lder cycloaddition between (鈭?-sabinene and o-quinone methide, which was generated from the corresponding o-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones 1鈥?b>8 against Coxsackie virus B3 were evaluated, and the primary structure鈥揳ctivity relationships were analyzed. Compound 3 was the most potent compound, with an IC₅₀ of 0.41 渭M.