Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus

Two triprenylated toluquinone and toluhydroquinone marine fungal metabolites, 5-methyl-2-[(2'E,6'E)-3',7',11-trimethyl-2',6',10'-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione and 5-methyl-2-[(2'E,6'E)-3,7,11-trimethyl-2',6',10'-dodecatrienyl]1,4-benzenediol, were synthesized in four and five steps, respectively, from 2-methyl-1,4-benzoquinone. The synthesis extends the applicability of the oxidative ether cleavage of hydroquitione dimethyl ethers with argentic oxide under acidic conditions to include the oxidative demethylation of polyprenylated-1,4-dimethoxy-toluhydroquinones with a quantitative survival of the oxidation- and acid-sensitive polyprenyl side chain. (c) 2006 Elsevier Ltd. All rights reserved.