Syntheses of oxidized metabolites implicated as active forms of the highly potent carcinogenic hydrocarbon dibenzo[ def, p]chrysene

Abstract

Polycyclic aromatic hydrocarbons (PAHs) are an important class of environmental carcinogens, and dibenzo[ def, p]chrysene is the most potent carcinogenic PAH currently known. Syntheses of various oxidized metabolites of dibenzo[ def, p]chrysene implicated as the biologically active forms that interact directly or indirectly with DNA to induce mutations that lead to tumor induction are reported. These include the 8,9- and 11,12-dihydrodiols ( 2 and 3), the 8,9,11,12- bis-dihydrodiol ( 5), and the fjord region anti-diol epoxide derivative of 3 (4).