A novel biomimetic synthesis of (S)-(−)-zearalenone: via macrocyclization and transannular aromatization

On heating, a hydroxy-keto-dioxinone underwent retro-Diels–Alder fragmentation and the resultant α,γ-diketo-ketene was efficiently trapped intramolecularly by a secondary alcohol to provide a macrocyclic triketo-lactone. Following ketal hydrolysis, transannular aromatization gave the resorcylate natural product, (S)-(−)-zearalenone.

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