(+)- and (–)-Benzo[a]pyrene 7,8-oxide : synthesis, absolute stereochemistry, and stereochemical correlation with other mammalian metabolites of benzo[a]pyrene
Abstract
Optically pure samples of (+)- and (–)-benzo[a]pyrene 7,8-oxide have been synthesized from the separated diastereoisomers of trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. The latter separation was effected by short-column chromatography–recrystallization or high pressure liquid chromatography. The absolute stereochemistry of (+)-trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzo[a]pyrene has been assigned as (7S,8S) by an X-ray crystal structure analysis; this structure has in turn been unequivocally correlated with the stereochemistry of (7S,8R)-(–)-benzo[a]pyrene 7,8-oxide and a range of mammalian metabolites.
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