NHC-catalyzed higher-order (5 + 3) cyclization for accessing tetracyclic eight-membered lactones

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-26 DOI:10.1016/j.tet.2025.134954

Ke-Xuan Tong , Shao-Qing Shi , Yin-Ping Liu, Wen-Juan Hao, Bo Jiang

引用次数: 0

Abstract

An oxidative N-heterocyclic carbene (NHC)-catalyzed higher-order (5 + 3) cyclization reaction starting from 2-indolylphenols and α,β-alkynals with the aid of Sc(OTf)₃ is reported, enabling the direct synthesis of tetracyclic 8-membered lactones bearing a bridged aryl-indole unit in moderate to good yields. This protocol exhibits a broad substrate scope, good compatibility with substituents and mild conditions, offering a modular organocatalytic approach for creating medium-sized lactones.

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nhc催化获得四环八元内酯的高阶（5 + 3）环化反应

报道了在Sc(OTf)3的催化下，以2-吲哚酚和α，β-炔醇为起始原料，由n -杂环羰基（NHC）催化的高阶（5 + 3）环化反应，可直接合成含桥接芳基-吲哚单元的8元四环内酯，产率中高。该方案具有广泛的底物范围，与取代基的良好相容性和温和的条件，为创建中等大小的内酯提供了模块化的有机催化方法。

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

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.