Design and Synthesis of Out/Out, Out/In, and In/In Epoxides in Polycyclic Cage Frameworks

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Synlett Pub Date : 2024-09-10 DOI:10.1055/a-2384-6736
Sambasivarao Kotha, Mohammad Salman
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引用次数: 0

Abstract

We report a useful synthetic approach to assemble in/in epoxide, in/out epoxide, and out/out epoxide in cage systems using the Corey–Chaykovsky reaction and the Peterson olefination as key steps. In this regard, a variety of pentacycloundecane (PCUD) based cage compounds containing oxirane rings with diverse stereochemical disposition were synthesized via a simple synthetic sequence. Five cage diones were used for this purpose, and the starting cage diones were prepared with easily accessible starting materials such as 1,4-hydroquinone derivatives and cyclopentadiene. Here, we have used the Diels–Alder (DA) reaction, a [2+2] photocycloaddition, the Corey–Chaykovsky reaction, and the Peterson olefination as crucial steps to prepare the target molecules.

Abstract Image

多环笼框架中外/内、外/内和内/内环氧化物的设计与合成
我们报告了一种有用的合成方法,该方法以 Corey-Chaykovsky 反应和 Peterson 烯化反应为关键步骤,在笼状体系中组装进/进环氧化物、进/出环氧化物和出/出环氧化物。为此,我们通过简单的合成顺序合成了多种基于五acycloundecane(PCUD)的笼状化合物,这些化合物含有具有不同立体化学布局的环氧乙烷环。为此,我们使用了五种笼型二元杂环化合物,起始笼型二元杂环化合物是用 1,4-氢醌衍生物和环戊二烯等容易获得的起始原料制备的。在这里,我们将 Diels-Alder (DA) 反应、[2+2] 光环加成反应、Corey-Chaykovsky 反应和 Peterson 烯化反应作为制备目标分子的关键步骤。
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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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