Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone

Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone
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通过羟基对醌的分子间 [5 2] 均二聚全合成 ()-Perezoperezone

DOI:
10.1002/anie.201911978
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发表时间:
2019-11-08
影响因子:
16.6
通讯作者:
Deng, Jun
Deng, Jun
中科院分区:
化学1区
文献类型:
--
作者:
Long, Yang;Ding, Yiming;Deng, Jun

文献摘要

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首次报道了铜催化的羟基对苯醌的分子间[5+2]同二聚反应,以典型的高产率和优异的非对映选择性提供了双环[3.2.1]辛二烯酮核心结构。应用这种合成方法能够从市售的3,5-二甲氧基甲苯进行简洁的九步全合成(-)-perezoperezone。
The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (-)-perezoperezone from commercially available 3,5-dimethoxytoluene.