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Syntheses of Minutuminolate and Related Coumarin Natural Products and Evaluation of Their TNF-α Inhibitory Activities.

ABSTRACT: 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.

SUBMITTER: Choo MZY

PROVIDER: S-EPMC10633832 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Syntheses of Minutuminolate and Related Coumarin Natural Products and Evaluation of Their TNF-α Inhibitory Activities.

Choo Malcolm Zheng Yuan MZY Khaw Lachelle Wei Ting LWT Chai Christina Li Lin CLL

ACS omega 20231023 44

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 t ...[more]

PMID: 37970054

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