Synthesis of trans-10,11-Dihydroxy-10,11-dihydrodibenz(a,h)acridine and Its Diastereomeric Epoxides. Possible Carcinogenic Metabolites of Dibenz(a,h)acridine

Article abstract of DOI:10.1021/jo00217a011

trans-10,11-Dihydroxy-10,11-dihydrodibenz(a,h)acridine (12), (+/-)-10α,11β-dihydroxy-8α,9α-epoxy-8,9,10,11-tetrahydrodibenz(a,h)acridine (3), and 10α,11β-dihydroxy-8β,9β-epoxy-8,9,10,11-tetrahydrodibenz(a,h)acridine (4), which are potentially proximate and ultimate carcinogens of dibenz(a,h)acridine (1), are synthesized.Regiospecific oxygenation at C-11 of 8,9,10,11-tetrahydrodibenz(a,h)acridine with mercuric acetate in acetic acid resulted in an intermediate that was converted to the above dihydrodiol and diol epoxides. 1H NMR, UV, and fluorescence emission spectra of dibenz(a,h)acridine derivatives are reported.