Ding Yiming, Long Xianwen, Zhang Jingwei, Qu Chunlei, Wang Peng, Yang Xiaodong, Puno Pema-Tenzin, Deng Jun
Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 China.
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University Tianjin 300071 China
Chem Sci. 2025 Apr 8;16(19):8302-8308. doi: 10.1039/d5sc01508a. eCollection 2025 May 14.
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 the benzyl aldehyde fragment facilitated a convergent formal [4 + 2] annulation with gregatin A, ultimately leading to the formation of penicifuranone A.
通过氮杂环卡宾（NHC）催化的极性反转策略，经八步反应完成了青霉呋喃酮A的首次不对称全合成。该合成的关键特征包括：通过铝-萨伦（Al-Salen）催化的不对称氰基硅烷化反应引入格雷加汀A的叔醇，以及氮杂环卡宾催化的施泰特-羟醛串联反应。苄基醛片段的极性反转策略促进了与格雷加汀A的汇聚式形式[4 + 2]环化反应，最终生成了青霉呋喃酮A。
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