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α-取代丙烯酸与亚砜叶立德的环化偶联反应:简便合成生物活性γ-丁内酯

Annulative coupling of α-substituted acrylic acids and sulfoxonium ylides: easy access to bioactive γ-butyrolactones.

作者信息

Kumar Naveen, Pandey Satyendra Kumar

机构信息

Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.

出版信息

Chem Commun (Camb). 2024 Aug 15;60(67):8872-8875. doi: 10.1039/d4cc03187c.

Abstract

We present a straightforward, catalyst- and additive-free method for synthesizing keto γ-butyrolactones using readily available β-keto sulfoxonium ylides and acrylic acids. This robust approach demonstrates exceptional compatibility with various functional groups on β-keto sulfoxonium ylides and α-substituted acrylic acids, resulting in good to high yields of the anticipated products. Moreover, the practicality of this approach was validated through large-scale reactions and the successful conversion of some synthesized derivatives into bioactive natural products, including L-factor, muricatacin, and cytosporanone A.

摘要

我们提出了一种直接的、无催化剂和添加剂的方法,该方法使用易于获得的β-酮亚磺酰基叶立德和丙烯酸来合成酮基γ-丁内酯。这种稳健的方法显示出与β-酮亚磺酰基叶立德和α-取代丙烯酸上的各种官能团具有出色的兼容性,从而使预期产物的产率良好至高。此外,通过大规模反应以及将一些合成衍生物成功转化为生物活性天然产物(包括L-因子、多氧霉素和孢菌素A),验证了该方法的实用性。

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