跨环酰化促进超穿孔素全合成中C5-C9键的形成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-26 DOI:10.1021/acs.orglett.5c0024310.1021/acs.orglett.5c00243

Julien A. König, Sebastian Frey, Bernd Morgenstern and Johann Jauch*,

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引用次数: 0

摘要

金丝桃素因其引人注目的复杂分子结构和显著的生物活性而被认为是多环多烯酰基酰基氯葡萄糖苷类化合物中的旗舰同系物，因此在过去二十年中成为化学家们极具吸引力的合成目标。本文报告了一种创新的金丝桃素线性全合成方法。我们的合成依赖于双环[3.3.1]壬烷-2,4,9-三酮框架的形成，该框架通过装饰八元环的反annular酰化作用形成，然后进行后期桥头取代。

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Transannular Acylation Facilitates C5–C9 Bond Formation in Hyperforin Total Synthesis

Hyperforin is considered the flagship congener among polycyclic polyprenylated acylphloroglucinols due to its compelling and complex molecular architecture, coupled with remarkable biological activity, thus rendering it an appealing synthetic target for chemists over the past two decades. Herein, an innovative linear total synthesis of hyperforin is reported. Our synthesis relies on the formation of the bicyclo[3.3.1]nonane-2,4,9-trione framework via transannular acylation of a decorated eight-membered ring, followed by late stage bridgehead substitution.

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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.