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A novel biomimetic synthesis of (S)-(−)-zearalenone: via macrocyclization and transannular aromatization |
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| Authors: | Hideki Miyatake-Ondozabal |
| Institution: | Department of Chemistry, Imperial College, London SW7 2AZ, UK |
| Abstract: | 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. |
| Keywords: | Resorcylic acid lactones Retro-Diels-Alder Intramolecular ketene trapping Transannular aromatization Biomimetic synthesis |
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