桔梗中(3R,4S)-6-乙酰-3-羟基-7-甲氧基-2,2-二甲基铬-4-基(Z)-2-甲基丁-2-烯酸酯的全合成及绝对构型的再确认

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-28 DOI:10.1021/acs.jnatprod.5c00269

Sanket S Shete, Swetha Balamurugan, D Srinivasa Reddy

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引用次数: 0

摘要

在此，我们报道了首次从Ageratina granfolia中分离的天然产物(3R,4S)-6-乙酰基-3-羟基-7-甲氧基-2,2-二甲基铬-4-基(Z)-2-甲基丁-2-烯酸酯的完全合成和绝对立体化学构型的确认。我们使用现成的间苯二酚作为起始原料，并建立了雅各布森不对称环氧化反应来实现全合成。在此过程中，我们制备了其对映体和位置异构体，这些异构体可能对生物学研究有用。

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Total Synthesis and Reconfirmation of the Absolute Configuration of (3R,4S)-6-Acetyl-3-hydroxy-7-methoxy-2,2-dimethylchroman-4-yl(Z)-2-methylbut-2-enoate Isolated from Ageratina grandifolia.

Herein, we report the first total synthesis and confirmation of the absolute stereochemical configuration of a natural product isolated from Ageratina grandifolia as (3R,4S)-6-acetyl-3-hydroxy-7-methoxy-2,2-dimethylchroman-4-yl(Z)-2-methylbut-2-enoate. We have used readily available resorcinol as a starting material and well-established Jacobson's asymmetric epoxidation in achieving the total synthesis. During this process, we prepared its enantiomers and positional isomers, which may be useful for biological studies.

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.