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Unprecedented reactivity between naphthoquinone and β‐aryl‐α‐keto acids has been uncovered. The process combined the redox properties of the Michael‐type naphthoquinone acceptor with arylpyruvic acid, which is acting first as a C3‐donor pro‐nucleophile and later as an acylating agent. As a result, densely substituted naphthofuran‐2(3H)‐ones were generated in a mild and simple one‐pot reaction.