Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide
Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide
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利用双官能锍/鏻叶立德合成α,β-不饱和环氧酮
DOI：
10.1039/d1cc02475b
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发表时间：
2021
影响因子：
4.9
通讯作者：
Tochtrop, Gregory P.
中科院分区：
文献类型：
--
作者：
Eskandari, Roozbeh;Hess, Jeremy P.;Tochtrop, Gregory P.
本文介绍了一种利用双功能硫/膦叶立德快速合成α，β-不饱和环氧酮的新方法。这种方法包括两个硫和膦叶立德和两个不同的醛之间的连续化学选择反应，允许快速构建各种不对称的α，β-不饱和环氧酮。这种方法允许快速构建一类脂质过氧化产物-环氧酮十八烯酸的核心反应官能团，但可以进一步广泛地用作合成天然产物的有用的合成子，特别是那些来自氧化脂肪酸的产物。因此，描述了一种利用该方法合成环氧酮十八烯酸分子家族的方案。
Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.