伞形酮
香豆素
天然产物
部分
化学
全合成
水解
组合化学
立体化学
有机化学
作者
Malcolm Zheng Yuan Choo,Lachelle Wei Ting Khaw,Christina L. L. Chai
出处
期刊:ACS omega
[American Chemical Society]
日期:2023-10-23
卷期号:8 (44): 41785-41791
标识
DOI:10.1021/acsomega.3c06361
摘要
The concise syntheses of the coumarin natural product, minutuminolate (1), and its related natural products, 7-methoxy-8-(2-acetoxy-3-methyl-1-oxobut-2-enyl) coumarin (2) and muralatin I (3), were accomplished for the first time in 4–5 steps from the commercially available umbelliferone. The key step involves a palladium-catalyzed oxidative rearrangement reaction to assemble the α-acyloxyenone moiety in 1 and 2. The incorporation of this functionality enables the successful synthesis of coumarin 3 through an acidic hydrolysis reaction. The anti-inflammatory activities of the compounds were also evaluated against tumor necrosis factor-alpha production in lipopolysaccharides-stimulated RAW264.7 cells. Our developed synthetic route will facilitate the development of analogues and derivatives of 1–3 with potent anti-inflammatory activities.
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