Total synthesis of (.+-.)-silybin, an antihepatotoxic flavonolignan.

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Abstract
The flavonolignan (.+-.)-silybin (1), having an antihepatotoxic activity, was synthesized via a key intermediate [3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde], which was prepared from readily available starting materials. The aldehyde (9) was transformed to the methoxymethyl ether, which was condensed with an acetophenone derivative to yield the chalcone. Oxidation of the chalcone with alkaline H2O2, followed by treatment of the resulting epoxide with HCl afforded (.+-.)-1.

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