Synthesis of bicyclo[4.2.0]octane ring of kingianin via [2+2] ketene cycloaddition

IF 17.7 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2024-03-25 DOI:10.25135/acg.oc.164.2402.3124

Mohamad Nurul Azmi Mohamad Taib, M. Litaudon, K. Awang, Yvan Six

引用次数: 0

Abstract

: Kingianins are pentacyclic polyketides isolated from Endiandra kingiana . They exhibit promising activity in inhibiting anti-apoptotic proteins (i.e Bcl-xL and Mcl-1) and anti-diabetic proteins (α-glucosidase) at micromolar levels. Due to their structural complexity and intriguing biological activity, researchers are increasingly focussing on designing total synthesis routes for these compounds. In this communication, we propose a new non-biomimetic synthesis strategy that utilises a [2+2] ketene cycloaddition reaction as a key-step to access the bicyclo[4.2.0]octane system of kingianins. To the best of our knowledge, this is the first report based on this approach.

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通过[2+2]烯酮环加成法合成金雀花素的双环[4.2.0]辛烷环

:Kingianins 是一种从 Endiandra kingiana 中分离出来的五环多酮化合物。它们在微摩尔水平抑制抗凋亡蛋白（即 Bcl-xL 和 Mcl-1）和抗糖尿病蛋白（α-葡萄糖苷酶）方面表现出良好的活性。由于这些化合物结构复杂且具有引人入胜的生物活性，研究人员越来越关注这些化合物的全合成路线的设计。在这篇通讯中，我们提出了一种新的非仿生合成策略，利用[2+2]烯酮环加成反应作为关键步骤来获得王烷苷的双环[4.2.0]辛烷体系。据我们所知，这是第一份基于这种方法的报告。

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

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.

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