Biomimetic Total Synthesis of (±)-Carbocyclinone-534 Reveals Its Biosynthetic Pathway

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2020-10-21 DOI:10.1021/acs.orglett.0c02865

Chunlei Qu, Xianwen Long, Yueqian Sang, Min Zhang, Xiaoli Zhao, Xiao-Song Xue*, Jun Deng*

引用次数: 3

Abstract

Carbocyclinone-534 is a new antibiotic produced after the metabolism of tapinarof. We identify a biomimetic total synthesis of carbocyclinone-534 in eight steps by taking advantage of an intermolecular Diels–Alder homodimerization/dehydrogenation/intramolecular Diels–Alder cycloaddition cascade. This synthetic sequence provides direct experimental evidence for revealing the biosynthetic pathway of carbocyclinone-534.

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(±)-碳环素-534的仿生全合成揭示了其生物合成途径

Carbocyclinone-534是由木薯粉代谢后产生的一种新型抗生素。我们利用分子间Diels-Alder同二聚/脱氢/分子内Diels-Alder环加成级联的八个步骤，确定了碳环素-534的仿生全合成。该合成序列为揭示碳环素-534的生物合成途径提供了直接的实验依据。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.