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Base-catalyzed self-condensation of 3,5-dimethoxyhomophthalic acid (2) directly furnished the 6,8-dimethoxy-3-(2′-carboxy-3′,5′-dimethoxyphenyl)methylisocoumarin (3) which on successive treatment with oxalyl chloride, diazomethane and hydrolysis afforded the corresponding 2′-acetylisocoumarin (5). Complete demthylation of the latter yielded the 6,8-dihydroxy-3-(2′-acetyl-3′,5′-dihydroxyphenyl)methylisocoumarin (6) related to the natural product feralolide (1a).
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