64314-00-7Relevant articles and documents
Resolution of polycyclic aromatic hydrocarbon dihydrodiols via diastereomeric formaldehyde acetals
Lakshman, Mahesh K.,Chaturvedi, Surendrakumar,Kole, Panna L.,Windels, James H.,Myers, Mark B.,Brown, Michael A.
, p. 3375 - 3378 (2007/10/03)
Diastereomeric formaldehyde acetals, formed from the reaction of racemic benzo[a]pyrene dihydrodiol and (-)-chloromethylmenthyl ether, are novel intermediates for effecting the convenient resolution of these metabolites by HPLC. This resolution technique seems generally applicable since the dihydrodiols of benzo[c]phenanthrene can also be readily resolved through this methodology. Key differences in the proton NMR spectra of the diastereomeric dihydrodiol menthyloxymethyl ethers have been identified which could be used for absolute stereochemical assignments.
Enantioselective synthesis of the tumorigenic anti-diol epoxide metabolites of benzo[a]pyrene
Harvey, Ronald G.
, p. 2737 - 2740 (2007/10/02)
Efficient, highly enantioselective syntheses of (+) and (-)-anti-benzo[a]pyrene diol epoxide (BPDE) from 9,10-dihydrobenzo[a]pyrene are described. Initial epoxidation catalyzed by (salen) Mn(III) complex gives 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (
(+)- and (-)-Benzopyrene 7,8-Oxide: Synthesis, Absolute Stereochemistry, and Stereochemical Correlation with Other Mammalian Metabolites of Benzopyrene
Boyd, Derek R.,Gadaginamath, Guru S.,Kher, Anil,Malone, John F.,Yagi, Haruhiko,Jerina, Donald M.
, p. 2112 - 2116 (2007/10/02)
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.