有效抑制p糖蛋白的大环脂肽二羟内酰胺A的合成及制备。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-16 DOI:10.1021/acs.joc.5c01765

Petros Danielsen Siapkaras,Karoline Hanssen,Eirik Johansson Solum,Marius Aursnes

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引用次数: 0

摘要

2019年，环脂肽dysoxyylactam A被分离出来，并被报道为药物外排泵p -糖蛋白的有效抑制剂，并显示出逆转癌细胞多药耐药的能力。在此，我们报告了一条可靠而灵活的途径，以实现对羟内酯a的转化，其中包括Paterson 1,2-抗醛醇反应、sp3-sp3 Fu-Suzuki偶联、不对称烯丙化和Corey-Nicolaou大内酯化。合成的天然产物的所有数据都与真品相符。

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Synthetic Preparation of the Macrocyclolipopeptide Dysoxylactam A for Potent P-glycoprotein Inhibition.

In 2019, the cyclolipopeptide dysoxylactam A was isolated and reported to be a potent inhibitor of the drug efflux pump P-glycoprotein and demonstrated the ability to reverse multidrug resistance in cancer cell lines. Herein, we report a reliable and flexible route toward dysoxylactam A, which features key transformations such as the Paterson 1,2-anti aldol reaction, an sp3-sp3 Fu-Suzuki coupling, asymmetric allylation, and the Corey-Nicolaou macrolactonization. All the data obtained on the synthesized natural product matched those of the authentic material.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.