A versatile synthesis of fumaquinone.
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.
Peña-López
Miguel
M
Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain.
Martínez
M Montserrat
MM
Sarandeses
Luis A
LA
Pérez Sestelo
José
J
D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D009285:Naphthoquinones; C502104:fumaquinone