Hughes Alexander J, Townsend Steven D
Department of Chemistry, Vanderbilt University, Nashville, TN-37235, United States.
Chemistry. 2024 Mar 12;30(15):e202303985. doi: 10.1002/chem.202303985. Epub 2024 Jan 23.
Herein, we describe the total synthesis of ervaoffine J & K from a central intermediate. Ervaoffine J was synthesized in eight steps in 14 % yield. Our strategy features an aerobic Winterfeldt oxidation to introduce the 4-quinolone moiety. Ervaoffine K was produced in ten steps and 10 % yield. The synthesis leveraged (bromodifluoromethyl)-trimethylsilane to induce a regioselective von Braun-type C-N bond fragmentation. This C-N bond cleavage unveiled the tetrasubstituted all-syn cyclohexane core of ervaoffine K and enabled the completion of its synthesis.
在此，我们描述了从一个关键中间体出发全合成埃瓦奥菲宁J和K的过程。埃瓦奥菲宁J经八步反应合成，产率为14%。我们的策略以需氧的温特费尔特氧化反应引入4-喹诺酮部分为特色。埃瓦奥菲宁K经十步反应合成，产率为10%。该合成利用（溴二氟甲基）-三甲基硅烷诱导区域选择性的冯·布劳恩型C-N键断裂。这种C-N键的裂解揭示了埃瓦奥菲宁K的四取代全顺式环己烷核心，并使其合成得以完成。
