Synthesis of potentially carcinogenic higher oxidized metabolites of dibenz(a,j)anthracene and benzo(c)chrysene

The terminal ring bis(dihydrodiol) derivatives of dibenz(a,j)anthracene and benzo(c)chrysene, as well as a number of higher oxidized derivatives of dibenz(a,j)anthracene, were conveniently synthesized. A key step of the synthetic route is double oxidative photocyclization of tetramethoxy-substituted diolefins. An alternative synthesis, which involves the reaction of the lithium salt of 1,4-dimethoxy-1,4-cyclohexadiene with 1,3-bis(iodoethyl)benzene to afford a bis-alkylated diketone which goes through cyclization to 3,11-diketododecahydrodibenz(a,j)anthracene, produced several higher oxidized derivatives of dibenz(a,j)anthracene.