Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-11-10 DOI:10.1016/j.tet.2024.134368

Gordon W. Gribble, Stephen W. Wright

引用次数: 0

Abstract

We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a sp² iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.

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从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的合成

我们描述了首次成功合成从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的过程，该过程使用了以前未报道过的α-溴酮与 sp2 碘化物在镍催化下的交叉亲电子偶联，从而提供了碳框架的趋同合成，且不会同时发生烯烃迁移。因此，吲哚生物碱是由已知化合物分两步合成的。

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.

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