Total synthesis of (+/-)-4'-demethylmacrophyllol, a naturally occurring compound

The naturally occurring compound 4'-Demethylmacrophyllol (1), 8-Hydroxy-3-(4-hydroxy-3,5-dimethoxy-phenyl)-isochroman-1-one, was synthesized starting from 4-benzyloxy-3,5-dimethoxybenzaldehyde (3) and a phosphonium salt (2) in four steps with an overall yield of 44%. This is the first report on the total synthesis of 4'-demethylmacrophyllol (1). The structures of compounds were determined by NMR and MS and elemental analysis techniques.