Diversification of (E,E)-1,6-Dioxo-2,4-Dienes for the Synthesis of (+)-Aspicillin, Isolaurepan, and β-Parinaric Acid,The Journal of Organic Chemistry

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Diversification of (E,E)-1,6-Dioxo-2,4-Dienes for the Synthesis of (+)-Aspicillin, Isolaurepan, and β-Parinaric Acid
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.joc.2c01280
Dattatraya H Dethe ₁ , Aparna Srivastava ₁ , Appasaheb K Nirpal ₁ , Nagabhushana C Beeralingappa ₁ , Vimlesh Kumar ₁ , Arsheed A Bhat ₁

Affiliation

A divergent formal synthesis of polyhydroxylated macrocyclic lactone (+)-aspicillin and polyene bioactive natural product β-parinaric acid and the total synthesis of non-terpenoid metabolite isolaurepan have been achieved using a ruthenium-catalyzed stereo- and chemoselective oxidative coupling reaction of easily accessible vinyl ketones and acrylates. The crucial transformation involves the efficient synthesis and functionalization of stereodefined (E,E)-1,6-dioxo-2,4-dienes using simple reaction protocols, which enabled straightforward access to a diverse range of bioactive natural products.

中文翻译：

(E,E)-1,6-Dioxo-2,4-Dienes 的多样化用于 (+)-Aspicillin、Isolaurepan 和 β-Parinaric 酸的合成

使用容易获得的钌催化的立体和化学选择性氧化偶联反应，实现了多羟基化大环内酯 (+)-阿司匹林和多烯生物活性天然产物 β-parinaric 酸的不同形式合成和非萜类代谢物异拉脲的全合成。乙烯基酮和丙烯酸酯。关键的转化涉及使用简单的反应方案对立体定义的 ( E,E )-1,6-dioxo-2,4-二烯进行有效合成和功能化，从而可以直接获得各种生物活性天然产物。

更新日期：2022-08-03

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