通过铜催化的三组分组装和金促进的6-内环环化，流线型模块化合成萨弗霉素亚结构。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-01-28 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.14

Asahi Kanno, Ryo Tanifuji, Satoshi Yoshida, Sota Sato, Saori Maki-Yonekura, Kiyofumi Takaba, Jungmin Kang, Kensuke Tono, Koji Yonekura, Hiroki Oguri

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引用次数: 0

摘要

铜(I)催化的三组分偶联与金(I)介导的6-内环环化相结合，简化了双-四氢异喹啉（THIQ）生物碱亚结构的快速模块化组装。具有2,3-二氨基苯并呋喃片段的关键合成中间体的设计允许金(I)介导的区域控制6-端氢胺化和腈和酚羟基的临时保护。该合成策略使含异喹啉和THIQ单元的saframycin亚结构的有效合成从三个组分的模块化组装只需四个步骤。我们还发现了一个意想不到的荧光中间体参与级联合成过程。

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Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization.

The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-endo hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.