Synthetic Studies on Suberosin and Osthol

Alternative syntheses of Suberosin (V) as well as Osthol (I) have been described. When the metal salts of 2-hydroxy-4-methoxybenzaldehyde (XI), such as Li, Na, K, Ca and Ti salt, were treated with γ, γ-dimethylallyl bromide in benzene and water, the four compounds, 3-γ, γ-dimethylallyl-2-hydroxy-4-methoxybenzaldehyde (IV), 5-γ, γ-dimethylally1- 2-hydroxy-4-methoxybenzaldehyde (VIII), 2-γ, γ-dimethylallyloxy-4-methoxybenzaldehyde (IX) and 2-γ, γ-dimethylallyl-5-methoxyphenol (X) were obtained.Furthermore, IX was converted to VIII by the thermal rearrangement of the γ, γ-dimethylallyl group.