Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds

4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck–Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel–Crafts acylation–DDQ dehydrogenation procedure to furnish 1.