Divergent Synthesis of Antiviral Diterpenes Wickerols A and B
Divergent Synthesis of Antiviral Diterpenes Wickerols A and B
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抗病毒二萜 Wickerols A 和 B 的不同合成
DOI：
10.1021/jacs.9b11838
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发表时间：
2020-03-11
影响因子：
15
通讯作者：
Gui, Jinghan
中科院分区：
文献类型：
--
作者：
Deng, Jiachen;Ning, Yuhan;Gui, Jinghan
Wickerols A和B是具有新型稠合6-5-6-6环骨架的二萜天然产物，并对H1N1 A型流感病毒表现出有效的抗病毒活性。在此，我们报告了一个发散的合成wickerols A和B，分别在16和15个步骤，从商业谷内酯。合成的关键反应是SmI 2介导的分子内酮-乙酸烯丙酯还原环化，Claisen重排和分子内烷基化/羟醛缩合反应，该反应以立体控制的方式快速组装紧凑的四环核心框架。本文所述的工作使我们能够确认wickerols A和B的绝对构型。
Wickerols A and B are diterpene natural products that have a novel fused 6-5-6-6 ring framework and exhibit potent antiviral activity against the H1N1 type A influenza virus. Herein, we report a divergent synthesis of wickerols A and B in 16 and 15 steps, respectively, from commercial sitolactone. The key reactions of the synthesis are a SmI2-mediated intramolecular ketone-allylic acetate reductive cyclization, a Claisen rearrangement, and an intramolecular alkylation/aldol reaction that rapidly assembled the compact tetracyclic core framework in a stereocontrolled manner. The work described herein allowed us to confirm the absolute configurations of wickerols A and B.