桃金娘酮A、C和桃金娘酮B-D的集体仿生合成。

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-06 DOI:10.1021/acs.orglett.5c01758

Zi-Jian Peng, Zhi-Zhang Duan, Xiao-Xia Chen, Wang-Ling Fang, Yi-Fan Liu, Zi-Zhe Cai, Jian-Guo Song, Xiao-Jun Huang, Wen-Cai Ye, Ying Wang, Li-Jun Hu

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引用次数: 0

摘要

我们报道了第一个非规范间苯三酚衍生物myrcauones A(1)和C(3)的集体仿生合成，具有独特的环状收缩间苯三酚骨架，以及三个生物合成相关的规范间苯三酚衍生物myrcauones B-D（4-6）。这些化合物从市售的3,4,5-三甲氧基苯酚开始，仅用6-9步合成。该合成策略的主要特点包括：杂环diels - alder反应构建规范间苯三酚骨架；α-酮重排驱动环收缩反应形成非规范间苯三酚骨架。

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Collective Biomimetic Synthesis of Myrcaulones A and C and Myrcauones B-D.

We report the first collective biomimetic synthesis of noncanonical phloroglucinol derivatives myrcaulones A (1) and C (3), featuring a unique ring-contracted phloroglucinol skeleton, along with three biosynthetically related canonical phloroglucinol derivatives myrcauones B-D (4-6). These compounds were synthesized in only 6-9 steps, starting from the commercially available 3,4,5-trimethoxyphenol. Key features of the synthetic strategy include a hetero-Diels-Alder reaction to construct the canonical phloroglucinol framework and an α-ketol rearrangement-driven ring contraction reaction to form the noncanonical phloroglucinol skeleton.

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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.