Formation of Fungal 2,18-Dioxo-2,18-seco Indole Diterpenes by Nonenzymatic Flavin-Catalyzed Oxidative Ring Expansion and Oxygen Incorporation from Solvent Water

文献类型： 外文期刊

第一作者： Dai, Yu

作者： Dai, Yu;Li, Shu-Ming;Xie, Xiu-Lan;Dai, Hao-Fu

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期刊名称：ORGANIC LETTERS （ 影响因子：5.2； 五年影响因子：4.9 ）

ISSN： 1523-7060

年卷期： 2023 年 25 卷 22 期

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收录情况： SCI

摘要： Most naturally occurring indole diterpenes share a 6/5/5/6/6/6hexacyclic ring system, while a 6/8/6/6/6 pentacyclic skeleton isoccasionally observed. In this study, we demonstrate the formationof an eight-membered C-N heteroring via nonenzymatic flavin-catalyzedoxidative indole ring opening. More interestingly, O-18-labeledexperiments proved that the two incorporated oxygen atoms are predominantlyoriginated from water instead of molecular oxygen. In this process,the oxidized form of flavin catalyzes two successive oxidations ofamines to imines with involvement of hydrolysis for the ring expansion.The reduced flavin is then regenerated by oxidation with molecularoxygen to form H2O2.

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