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Synthesis of Violaceic Acid and Related Compounds through Aryl Triazene

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journal contribution
posted on 16.02.2017, 13:07 authored by Shin Ando, James Burrows, Kazunori Koide
MPC1001 is a potent anticancer natural product that contains a violaceic acid moiety. Herein we report the total synthesis of the natural product violaceic acid and its derivative. In this approach, a triazene-directed Ullman coupling proved to be highly effective. We converted the triazene to a hydroxy group by means of a palladium-catalyzed reaction. Treatment of the triazene with trifluoroacetic acid generated an arenediazonium ion that produced an aryl radical, leading to the protodediazoniation and a tricyclic product.