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Synthesis of Spiro[4.5]ecanes by Au(I)‐Catalyzed Vinylogous Conia Ene Reaction

Fuhai Liu, Zhongting Ruan,Xiaoguang Duan,Ruize Ma, Xujuan Su,Ning Liang,Xingang Xie, Xuegong She

European Journal of Organic Chemistry(2023)

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Abstract
Au(I) catalysed vinylogous Conia ene reaction was developed to construct the densely functionalized spiro[4.5]-deca-1,6-diene-8-ones from easily available 4-alkyne tethered cyclohex-2-enones. 17 substrates with multiple substitutes on the cyclohex-2-enone ring were explored to afford the corresponding spiro[4.5]in 52-81 % yields. This reaction features mild conditions, wide substrate scope and atom economic characters. Au(I) catalysed vinylogous Conia ene reaction was developed to construct the spiro[4.5]-deca-1,6-diene-8-ones. The spirocyclization reaction was applied to rapidly construct the tetracyclic skeleton of ganocin C.image
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Key words
Au catalysis,ganocin C,spiro[4.5],synthetic methods
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