5,10-秒-新安霉素A的不对称全合成。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-08 DOI:10.1021/acs.orglett.5c02111

Huacheng Xu, Cheng Zou, Adila Nazli, Yuanwei Dai, Yun He* and Xiao-Shui Peng*,

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引用次数: 0

摘要

第一个不对称全合成5,10-seco-neoansamycin A，一个19元的环八肽，实现了20步（几个步骤被伸缩）和6.7%的总产率，从而导致其绝对构型的分配。这种聚合合成方法的特点是后期大内酰胺化，明智地应用了不对称醛醇反应。这项工作将为其他ansamycin天然产物的合成和5,10-seco-neoansamycin A作为潜在抗癌先导物的探索提供便利。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric Total Synthesis of 5,10-seco-Neoansamycin A

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Asymmetric Total Synthesis of 5,10-seco-Neoansamycin A

The first asymmetric total synthesis of 5,10-seco-neoansamycin A, a 19-membered cyclic octaketide, was achieved in 20 steps (with several steps being telescoped) and 6.7% overall yield starting from the reported compound, thus leading to the assignment of its absolute configuration. This convergent synthetic approach features late-stage macrolactamization, a judicious application of an asymmetric aldol reaction. This work will facilitate the synthesis of other ansamycin natural products and the explorations of 5,10-seco-neoansamycin A as a potential anticancer lead.

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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.