Synthesis of naturally occurring partial methyl ethers of myricetin

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The synthesis of combretol, annulatin, and europetin—naturally occurring partial methyl ethers of myricetin—is described. Condensation of 2, 4, 6-trihydroxy-ω-methoxyacetophenone with tri-O-methyl galloyl chloride or tri-O-benzyl galloyl chloride furnished the appropriate 3-methoxyflavones, which by a series of reactions furnished the natural myricetin derivatives.