Brevianamide S的全合成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-28 DOI:10.1021/acs.orglett.5c0086010.1021/acs.orglett.5c00860

Adam R. Lockyer, Helen E. Jones, Nicholas J. Green, Robert C. Godfrey, Vera P. Demertzidou, Gary S. Nichol and Andrew L. Lawrence*,

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引用次数: 0

摘要

通过8个步骤首次合成了生物碱brevianamide S。这种天然产物，从花色曲霉中分离出来，对卡介苗（BCG）具有选择性抗菌活性，卡介苗是一种常用的结核分枝杆菌替代物。Brevianamide S被认为通过一种尚未阐明的新机制起作用，使其成为开发下一代抗结核药物的有希望的先导药物。我们的方法采用双向合成策略，包括一个定制的烯基-烯基斯蒂尔交叉偶联反应和双醛醇缩合。这为未来合成结构多样的类似物提供了一个灵活有效的平台。

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Total Synthesis of Brevianamide S

The first total synthesis of the alkaloid brevianamide S has been achieved in eight steps. This natural product, isolated from Aspergillus versicolor, exhibits selective antibacterial activity against Bacille Calmette-Guérin (BCG), a commonly used surrogate for Mycobacterium tuberculosis. Brevianamide S is proposed to act through a novel, yet-to-be-elucidated mechanism, making it a promising lead in the development of next-generation antitubercular agents. Our approach employs a bidirectional synthetic strategy, involving a bespoke alkenyl–alkenyl Stille cross-coupling reaction and a double aldol condensation. This represents a flexible and efficient platform for the future synthesis of structurally diverse analogues.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.