Late-Stage C–H Functionalization of Dehydroalanine-Containing Peptides with Arylthianthrenium Salts and Its Application in Synthesis of Tentoxin Analogue

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-14 DOI:10.1021/acs.orglett.4c04535

Xing-Xing Ding, Bing-Tong Li, Lin Dong

引用次数: 0

Abstract

Dehydrophenylalanine has a characteristic unsaturated double bond that makes it indispensable in the context of peptides and proteins. In this study, we report the Pd-catalyzed C(sp²)–H arylation of dehydroalanine-containing peptides with arylthianthrenium salts under mild and base free conditions, which provides efficient access to dehydrophenylalanine-containing peptides. This approach enables the efficient coupling of different drug scaffolds and bioactive molecules to the peptides. Remarkably, the method could be used for the concise synthesis of tentoxin and its analogue.

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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.