
Journal of Organic Chemistry p. 356 - 360 (1993)
Update date:2022-09-26
Topics:
Young, Robert J.
Cortez, Cecilia
Luna, Ernestina
Lee, Hongmee
Harvey, Ronald G.
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.
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