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.
H. H. Lee and C. H. Tan, J. Chem. Soc. C, 1967, 1583 DOI: 10.1039/J39670001583
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