A versatile synthesis of fumaquinone

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.


J. Org. Chem. 2010, 75, 5337–5339 (DOI: 10.1021/jo100779z).

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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.