Stereoselective Synthesis of Biology-Oriented Pentacyclic Pyrrolo[2,1-a]isoquinoline Scaffolds by Photoredox-Induced Radical Annulations

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-25 DOI:10.1021/acs.orglett.5c00277

Zi-Qi Yi, Wenhui Zhang, Bing Yi, Chang Liu, Yanjun Xie, Maoqing Li, Yi Xiong, Weidong Wu, Jian-Ping Tan

引用次数: 0

Abstract

We report a visible-light photoredox-induced stereoselective radical 1,3-dipolar cycloaddition between tetrahydroisoquinolines and coumarin derivatives, providing a platform for the efficient synthesis of pseudo-natural-inspired fused pentacyclic scaffolds. Using this protocol, a diverse range of valuable fused pentacyclic pyrrolo[2,1-a]isoquinolines were efficiently obtained in moderate to good yields and excellent diastereoselectivities. Mechanistic investigations including radical control experiments and light on/off studies indicated that the reaction underwent a visible-light induced radical process. The insights gained from our studies are expected to advance general efforts toward the green synthesis of biology-oriented pseudo-natural products and heterocyclic skeletons.

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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.