Total Synthesis of Ervaoffine J and K

Abstract 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.