汉城链霉素的合成研究
收稿日期: 2024-10-13
修回日期: 2024-12-05
网络出版日期: 2024-12-20
基金资助
大学教育资助委员会-研资局(香港)(C6022-22W); 大学教育资助委员会-研资局(香港)(16300921); 大学教育资助委员会-研资局(香港)(16308922); 大学教育资助委员会-研资局(香港)(16304023)
Synthetic Studies towards Streptoseomycin
Received date: 2024-10-13
Revised date: 2024-12-05
Online published: 2024-12-20
Supported by
Research Grants Council, University Grants Committee of Hong Kong(C6022-22W); Research Grants Council, University Grants Committee of Hong Kong(16300921); Research Grants Council, University Grants Committee of Hong Kong(16308922); Research Grants Council, University Grants Committee of Hong Kong(16304023)
汉城链霉素属于大环内酯类的柚皮素家族, 具有有效的抗菌活性. 由于分子结构复杂, 汉城链霉素的全合成尚未见报道. 报道了我们在构建三环核心方面所做的工作, 该三环核心具有跨顺式十氢萘的醚桥, 具有汉城链霉素的所有必需功能. 其关键的合成策略依赖于苯醌与Danishefsky二烯的Diels-Alder反应、分子内Michael加成和分子内SN2醚化. 三环核心的构建不仅揭示了许多意想不到的转化, 而且为汉城链霉素的全合成奠定了坚实的基础.
关键词： 大环内酯; 十氢萘; Diels-Alder反应; 汉城链霉素
金令愚 , 童荣标 . 汉城链霉素的合成研究[J]. 有机化学, 2025 , 45(3) : 933 -944 . DOI: 10.6023/cjoc202409011
Streptoseomycin belongs to the nargenicin family of macrolides with potent antibacterial activity. Due to the complex molecular structure, total synthesis of streptoseomycin has not been reported. Herein, our efforts on construction of the tricyclic core featuring ether-bridge across the cis-decalin with all requisite functionalities for streptoseomycin are reported. The key synthetic strategy relies on Diels-Alder reaction of benzoquinone with Danishefsky diene, intramolecular Michael addition, and intramolecular SN2 etherification. Our successful construction of this tricyclic core not only uncovered many unexpected transformations but also laid a solid ground for the total synthesis of streptoseomycin.
Key words： macrolide; decalin; Diels-Alder reaction; streptoseomycin
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