两种环丁烷基非多环聚戊烯基间苯三酚高氮酮A和B的分离及仿生半合成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-09 DOI:10.1021/acs.orglett.4c0413510.1021/acs.orglett.4c04135

Xue-Yan Li, Lv-Jun Zhang, Yue-You Yang, Wei-Jia Lu, Sheng-Tao Ye, Hao Zhang, Ling-Yi Kong* and Wen-Jun Xu*,

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引用次数: 0

摘要

从金丝桃中发现了 Hyperzrones A (1) 和 B (2)，它们是两种前所未有的具有特征环丁烷分子的非多环丙烯酰化酰基氯葡萄糖醇。通过大量光谱分析、X 射线晶体学和量子化学计算方法确定了它们的结构。从天然前体金丝桃素 B（3）中实现了 1 和 2 的生物半合成，其特点是 Favorski 型重排和可见光介导的 [2 + 2] 光环加成。此外，还获得了几种不同的衍生物，为生物学研究提供了一个化合物库。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Isolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from Hypericum beanii

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Isolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from Hypericum beanii

Hyperzrones A (1) and B (2), two unprecedented nor-polycyclic polyprenylated acylphloroglucinols with a characteristic cyclobutane moiety, were discovered from Hypericum beanii. Their structures were determined by extensive spectroscopic analysis, X-ray crystallography, and quantum chemical calculation methods. A bioinspired semisynthesis of 1 and 2 was achieved from the natural precursor hypercalin B (3), featuring a Favorskii-type rearrangement and a visible-light-mediated [2 + 2] photocycloaddition. Several diverse derivatives were also obtained, providing a compound library for biological studies.

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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.