通过[Au]催化的硝基炔环异构化和分子内[3 + 2]-环加成尝试合成奥斯特酰胺的中心 2,2-二取代假吲哚核心

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-10-10 DOI:10.1016/j.tet.2024.134301

Swapnil V. Halnor, Chepuri V. Ramana

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引用次数: 0

摘要

在本文中，我们描述了一种金催化的硝基炔环异构化过程，预计该过程将构建天然产物 Austamide 的中心 2,2-二取代假吲哚基核心。我们打算采用硝基炔环异构化，然后进行分子内[3 + 2]环加成的方法来形成假吲哚基核心。然而，[3 + 2]环加成以不希望的方式发生，最终导致了复杂的六环支架。

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Attempted synthesis of the central 2,2-disubstituted pseudoindoxyl core of Austamide via a [Au]-catalyzed nitroalkyne cycloisomerization and intramolecular [3 + 2]-cycloaddition

Herein, we describe an Au-catalyzed cycloisomerization process of a nitroalkyne that was projected to construct the central 2,2-disubstituted pseudoindoxyl core of the natural product Austamide. Our intended strategy for forging the pseudoindoxyl core is based on the nitroalkyne cycloisomerization followed by a subsequent intramolecular [3 + 2] cycloaddition. However, the [3 + 2] cycloaddition occurred in an undesired manner, ultimately leading to a complex hexacyclic scaffold.

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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.