Fjord Region 3,4-Diol 1,2-Epoxides and Other Derivatives in the 1,2,3,4- and 5,6,7,8-Benzo Rings of the Carcinogen Benzochrysene

Article abstract of DOI:10.1021/jo00234a013

Dihydrodiol and diol epoxide derivatives of the carcinogen benzochrysene (BgCh) have been prepared to probe structural factors involved in the carcinogenesis and mutagenesis of polycyclic aromatic hydrocarbons.Preparation of 1,2-dihydrobenzochrysen-4(3H)-one (6) and 7,8-dihydrobenzochrysen-5(6H)-one (11), ketones suitable for further elaboration to potential metabolites of benzochrysene in the 1,2,3,4- and 5,6,7,8-benzo rings, respectively, was achieved through two cyclization steps.Photochemical closure of 2-(1- or 2-naphthyl)styrene derivatives 4 and 9 aff orded chrysene and benzophenanthrene ring systems with a butyric ester/acid side chain poised for a second ring closure (acid-catalyzed) to the desired ketones.Preparation of pure BgCh 3,4-diol 1,2-epoxides 23 and 24 from the dihydrodiol diester 14 by conversion to separable trans bromohydrins, cyclization to the epoxides, and hydrolysis of the acetates was found to be more successful than preparation from the dihydrodiol 15.