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双环[2.2.2]辛烯酮的氧化裂解:解开α-二甲氧基羰基

Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl.

作者信息

Yao Ting-Zhi, Tseng Yi-Cheng, Li Jia-Luo, Hou Deng-Lian, Chuang Gary Jing

机构信息

Department of Chemistry, Chung Yuan Christian University, Chung-Li 320314, Taiwan.

出版信息

J Org Chem. 2025 Feb 7;90(5):2126-2131. doi: 10.1021/acs.joc.4c02699. Epub 2025 Jan 28.

Abstract

This study explores the selective oxidative scission of bicyclo[2.2.2]octenones derived from masked -benzoquinones (MOBs). By employing the fragmentation of ketoximes and Schmidt-type reactions, we achieved the cleavage of α-dimethoxy carbonyl groups to yield highly functionalized cyclohexene frameworks, showcasing the expanding synthetic utility of bicyclo[2.2.2]octenones in complex organic synthesis. The methodologies developed are anticipated to contribute to advancements in organic and pharmaceutical chemistry.

摘要

本研究探索了源自掩蔽苯醌(MOBs)的双环[2.2.2]辛烯酮的选择性氧化裂解。通过利用酮肟的碎片化反应和施密特型反应,我们实现了α-二甲氧基羰基的裂解,生成了高度官能化的环己烯骨架,展示了双环[2.2.2]辛烯酮在复杂有机合成中不断扩大的合成效用。所开发的方法有望为有机化学和药物化学的发展做出贡献。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95da/11812015/24066eccd0d3/jo4c02699_0001.jpg

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