title: Biomimetic synthesis of resorcylate natural products utilizing late stage aromatization: concise total syntheses of the marine antifungal agents 15G256iota and 15G256beta.
abstract: Diketo-1,3-dioxin-2-ones underwent retro-Diels-Alder reaction on heating in toluene at 110 degrees C to generate alpha,gamma,-triketo-ketenes. These were trapped with alcohols to provide 2,4,6-triketocarboxylates, which were smoothly aromatized by sequential reaction with potassium carbonate and methanolic hydrogen chloride to give resorcylate esters. The reaction was applied in the total synthesis of the marine antifungal agents 15G256beta (1), 15G256iota (2), and 15G256pi (3) and the mycotoxin S-(-)-zearalenone (4).
authors.affiliation: Department of Chemistry, Imperial College London, London SW7 2AZ, England.
authors.forename: Ismael
authors.initials: I
authors.lastname: Navarro
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Basset
authors.forename: Séverine
authors.initials: S
authors.lastname: Hebbe
authors.forename: Sarah M
authors.initials: SM
authors.lastname: Major
authors.forename: Thomas
authors.initials: T
authors.lastname: Werner
authors.forename: Catherine
authors.initials: C
authors.lastname: Howsham
authors.forename: Jan
authors.initials: J
authors.lastname: Bräckow
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D032701:Biomimetics / Q000379:methods*; D004147:Dioxins / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D012118:Resorcinols / Q000138:chemical synthesis; D015025:Zearalenone / Q000138:chemical synthesis
chemical_list: C531522:15G256iota; D000935:Antifungal Agents; D001688:Biological Products; D004147:Dioxins; D004952:Esters; D007659:Ketones; D018942:Macrolides; D012118:Resorcinols; D015025:Zearalenone