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Abstract
Bay-region diol epoxides are assumed to be ultimate metabolites responsible for the mutagenic and carcinogenic actions of polycyclic aromatic hydrocarbons (PAH). They exhibit enhanced activity when they are in a more sterically hindered environment. Such a situation exists in the fjord-region of dibenzo[a,l]pyrene (DB[a,l]P). This compound was chosen to study this enhanced activity in comparison to that of benzo[a]pyrene. Authentic samples of the proposed metabolites of DB[a,l]P, (±)−trans−DB[a,l]P diol (1), (±)−anti−DB[a,l]P diol epoxide (DE) (2) and (±)−syn−DB[a,l]PDE (3), have been synthesized. The key intermediate 12−methoxy-DB[a,l]P (4) was successfully obtained by cyclization of 6−(3−methoxybenzyl)benzanthrone (5) with methanesulfonic acid. In turn (5) was prepared by 1,4 conjugate addition of 3−methoxybenzyl magnesium bromide to benzanthrone. The presence of the DB[a,l]P nucleus in DB[a,l]Pdiol (1) and DB[a,l]PDEs (2) and (3) was proven by conversion of (4) into the parent hydrocarbon in several steps.