Synthesis of the Active Dihydrodiol and Diol Epoxide Matabolites of the Steroid-Related Carcinogen 15,16-Dihydrocyclopentaphenanthrene and Its 11-Methyl Derivative

Article abstract of DOI:10.1021/jo00054a017

Cyclopentaphenanthrenes are a class of environmentally occurring carcinogens that are structurally related to sterols.While the parent hydrocarbon is biologically inactive, its 11-methyl and 17-keto derivatives are relatively potent carcinogens.Recent research has identified trans-3,4-dihydrodiol metabolites as the metabolic precursors of the corresponding anti- and/or syn-diol epoxides, implicated as the ultimate carcinogenic forms that bind to DNA.We now report the synthesis of the trans-3,4-dihydrodiol derivatives of cyclopentaphenanthrene and 11-methylcyclopentaphenanthrene, 3a and 3b, respectively, and the corresponding anti- and syn-diol epoxides of each of these hydrocarbons, 4a, 4b and 5a, 5b, respectively.Syntheses of the analogous trans-3,4-dihydrodiol metabolites of the 17-keto derivatives of cyclopentaphenanthrene and 11-methylcyclopentaphenanthrene are described in the accompanying paper.