Synthesis of linderone and methyl-inderone

Abstract

4′-Benzyloxy-2′-hydroxy-3′,5′,6′-trimethoxychalcone has been converted in three steps into 2,6-dihydroxy-3-methoxy-5-(β-phenylpropionyl)-1,4-benzoquinone which undergoes ring-contraction in the presence of aqueous alkali to give demethyldihydrolinderone. Methylation of this followed by dehydrogenation afforded methyl-linderone and hence linderone.