Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia.
Georganics Ltd., Koreničova 1, SK-811 03 Bratislava, Slovakia.
Int J Mol Sci. 2023 Jun 19;24(12):10331. doi: 10.3390/ijms241210331.
A versatile strategy for the enantioselective synthesis of a benzo[]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D () were achieved. Four stereoisomers, , -, and -, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.
开发了一种用于包含天然次级代谢产物的苯并[ ]氧杂环庚烷结构核心的对映选择性合成的通用策略。该合成方法的关键步骤包括用于构建七元环的闭环烯键复分解反应、用于安装双键的Suzuki-Miyaura 交叉偶联反应以及用于引入手性中心的 Katsuki-Sharpless 不对称环氧化反应。实现了杂Cornol D()的首次全合成和绝对构型指定。以 2,6-二羟基苯甲酸和二乙烯基甲醇为起始原料，制备了该天然聚酮的四个立体异构体， ，-，-和-。通过单晶 X 射线分析确定了杂Cornol D 的绝对和相对构型。通过将内酯的醚基还原方法应用于该合成方法，进一步展示了该合成方法的扩展，通过该方法合成了杂Cornol C。
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