Abstract
Sophoradin (I) [2′,4,4′-trihydroxy-3,3′,5-tris(3-methyl-2-buteny)chalcone] was synthesized through Claisen-Schmidt condensation followed by demethoxymethylation.Isoprenylation of p-hydroxybenzaldehyde with 3,3-dimethylallyl bromide in 10% potassium hydroxide solution gave 4-hydroxy-3,5-bis(3-methyl-2-butenyl)benzaldehyde (IX). Methoxymethylation of 2,4-dihydroxy-3-(3-methyl-2-butenyl)acetophenone (IV) and IX afforded 4-methoxymethoxy-IV (XVIII) and 4-methoxymethoxy-IX (XX). Condensation of XVIII and XX in 50% potassium hydroxide solution gave 2′-hydroxy-4,4′-bis(methoxymethoxy)-3,3′,5-tris(3-methyl-2-butenyl)chalcone (XXII). Hydrolysis of XXII with methanolic hydrochloric acid gave I which was identified with natural I by mixed mp, and IR and NMR spectra.
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