title: A versatile synthesis of fumaquinone.
abstract: Fumaquinone, a novel prenylated naphthoquinone antibiotic, was synthetized from ethyl acetoacetate in three steps (58% overall yield). The key step of the synthesis is the construction of the naphthoquinone skeleton by a regioselective Diels-Alder reaction between a 2-alkyl 1,3-bis(trimethylsilyloxy)-1,3-diene derivative and a bromoquinone. This short and versatile approach confirms the structure of fumaquinone and allows the synthesis of derivatives at the C-6 position.
authors.affiliation: Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain.
authors.forename: Miguel
authors.initials: M
authors.lastname: Peña-López
authors.forename: M Montserrat
authors.initials: MM
authors.lastname: Martínez
authors.forename: Luis A
authors.initials: LA
authors.lastname: Sarandeses
authors.forename: José
authors.initials: J
authors.lastname: Pérez Sestelo
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D009285:Naphthoquinones; C502104:fumaquinone