Journal of the Chemical Society. Perkin transactions I p. 2112 - 2116 (1980)
Update date:2022-09-26
Topics:
Boyd, Derek R.
Gadaginamath, Guru S.
Kher, Anil
Malone, John F.
Yagi, Haruhiko
Jerina, Donald M.
Optically pure samples of (+)- and (-)-benzopyrene 7,8-oxide have been synthesized from the separated diastereisomers of trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzopyrene.The latter separation was effected by short-column chromatography-recrystallisation or high pressure chromatography.The absolute stereochemistry of (+)-trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzopyrene 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)-(-)-benzopyrene 7,8-oxide and a range of mammalian metabolites.
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