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Updated: Jul 6, 2025

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Total Synthesis of Ervaoffine J and K
Alexander J Hughes1, Steven D Townsend1
1Department of Chemistry, Vanderbilt University, Nashville, TN-37235, United States.
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.
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