FLUORINE-SUBSTITUTED DERIVATIVES OF THE CARCINOGENIC DIHYDRODIOL AND DIOL EPOXIDE METABOLITES OF 7-METHYLBENZ[A]ANTHRACENE, 12-METHYLBENZ[A]ANTHRACENE AND 7,12-DIMETHYLBENZ[A]ANTHRACENE

Stereospecific syntheses of the trans-3,4-dihydrodiol metabolites of 9 - and 10-fluoro-7,12-dimethylbenz[a]anthracene, -7-methylbenz[a]anthra cene, and -12-methylbenz[a]anthracene are described, These dihydrodiol s are putative proximate carcinogenic metabolites that undergo activat ion by the P-450 microsomal enzymes to ultimate carcinogenic anti- and syn-diol epoxide metabolites that bind to nucleic acids in vivo. Synt heses of several of the anti- diol epoxide metabolites are also descri bed. (C) 1997 Elsevier Science Ltd.