Total Synthesis of (-)-Oridonin: An Interrupted Nazarov Approach
Total Synthesis of (-)-Oridonin: An Interrupted Nazarov Approach
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DOI：
10.1021/jacs.9b12034
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发表时间：
2019-12-25
影响因子：
15
通讯作者：
Luo, Tuoping
中科院分区：
文献类型：
--
作者：
Kong, Lingran;Su, Fan;Luo, Tuoping
基于关键的中断的纳扎罗夫反应，完成了(-)-冬凌草甲素的对映选择性全合成。首次探索了Nazarov/Hosomi-Sakurai级联的立体化学，以锻造具有挑战性的季碳的四环骨架。通过一系列精细的两环重排和后期氧化还原操作，实现了这一高度氧化的金龙烷类化合物的从头合成。
An enantioselective total synthesis of (-)-oridonin is accomplished based on a key interrupted Nazarov reaction. The stereochemistry of the Nazarov/Hosomi-Sakurai cascade was first explored to forge a tetracyclic skeleton with challenging quaternary carbons. A delicate sequence of two ring-rearrangements and late stage redox manipulations was carried out to achieve the de novo synthesis of this highly oxidized ent-kauranoid.