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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.

The unsymmetrical 3,4,8,9-bis(dihydrodiol) and the 10- and 11-phenolic trans-3,4- dihydrodiols of dibenz(a,j)anthracene were efficiently synthesized. The synthetic approach involves as key steps the asymmetric dihydroxylation of a stilbene precursor using a Sharpless catalyst and intramolecular cyclodehydrobromination catalyzed by Pd(PPh3)2Cl2. Good yields were obtained in all 13 steps of the synthesis of 3,4,8,9-bis(dihydrodiol) except one, with the overall yield placed at 17%.