Asymmetric Total Synthesis of Penicilfuranone A through NHC-Catalyzed Umpolung

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-04-08 DOI:10.1039/d5sc01508a

Yiming Ding, Xianwen Long, Jingwei Zhang, Qu Chunlei, Peng Wang, Xiaodong Yang, Pema-Tenzin Puno, Jun Deng

引用次数: 0

Abstract

The first asymmetric total synthesis of penicifuranone A was accomplished in eight steps through an NHC-catalyzed umpolung strategy. Key features of the synthesis include an Al-Salen catalyzed asymmetric cyanosilylation to install the tertiary alcohol of gregatin A, and an NHC catalyzed Stetter-Aldol cascade reaction. The umpolung strategy of benzyl aldehyde fragment facilitated a convergent formal [4+2] annulation with gregatin A, ultimately leading to the formation of penicifuranone A

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nhc催化Umpolung不对称合成青霉素呋喃酮A

第一次不对称全合成青霉素醌A是通过nhc催化的umpolung策略完成的，共八个步骤。该合成的主要特征包括Al-Salen催化的不对称氰基硅化反应，以安装gregatin A的叔醇，以及NHC催化的steter - aldol级联反应。苄基醛片段的umpolung策略促进了与聚甲素a的会聚形式[4+2]环，最终导致青霉素醌a的形成

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.