A short and efficient synthesis of cytotoxic 3-isopropylnaphthalene-1,2-dione via 3-hydroxy-2-naphthoic acid

3-Isopropylnaphthalene-1,2-dione (1) was synthesized from 3-hydroxy-2-naphthoic acid (5) in 4 steps (59% overall yield). After conversion of 5 to its methyl ester derivative, the crucial steps of the synthesis were the treatment of the ester with 4 eq MeMgI and then Pd-C catalyzed hydrogenation to give 3-isopropylnaphthalen-2-ol (8). Oxidation of 8 with m-chloroperbenzoic acid gave 1 in good yield.