(+)- and (–)-Benzo[a]pyrene 7,8-oxide : synthesis, absolute stereochemistry, and stereochemical correlation with other mammalian metabolites of benzo[a]pyrene
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2112-2116
- https://doi.org/10.1039/p19800002112
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.This publication has 1 reference indexed in Scilit:
- Synthesis of (+)- and (–)-naphthalene and anthracene 1,2-oxidesJournal of the Chemical Society, Perkin Transactions 1, 1979