硅酸烯六烯骨架的全合成及立体化学建议

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-04 DOI:10.1021/acs.orglett.4c04750

Maximilian Guhlke, Johannes Herbst, Tra Giang Nguyen, Andreas Schneider, Jeroen S. Dickschat, Dirk Menche

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引用次数: 0

摘要

通过改进双金属试剂的合成和高效的立体选择性多烯生成方案，采用迭代交叉耦合策略制备了含有三个z构型烯烃的不稳定多烯抗生素杆菌烯的中心六烯核心，具有优异的几何纯度，揭示了杆菌烯不稳定性的起源。此外，本文还报道了紫外-可见位移分析和生物合成基因聚类分析的绝对立体化学特征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Total Synthesis and Stereochemical Proposal of the Hexaene Framework of Bacillaene

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Total Synthesis and Stereochemical Proposal of the Hexaene Framework of Bacillaene

The central hexaene core of the labile polyene antibiotic bacillaene bearing three Z-configured olefins was prepared with excellent geometrical purity by an iterative cross-coupling strategy, involving improved syntheses of bimetallic reagents and efficient protocols for stereoselective polyene generation, revealing insights into the origin of bacillaene’s instability. Furthermore, a useful method for monitoring polyene iteration by UV–vis shift analyses and the absolute stereochemistry of this core by biosynthetic gene cluster analysis are reported.

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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.