68906-75-2Relevant academic research and scientific papers
Enantioselective Synthesis of the (+)-anti-7,8-Dihydrodiol-9,10-epoxide of the Potent Carcinogen Benzopyrene
Huang, Xiaoming,Harris, Thomas M.
, p. 1699 - 1700 (1995)
The title compound, the most important genotoxic metabolite of benzopyrene, has been prepared efficiently in a synthesis which capitalized on Jacobsen-type enantioselective epoxidation of 9,10-dihydrodibenzopyrene, cleavage of the epoxide by KOH-Me2SO to give the tetrahydro-trans-7,8-diol, and formation of the dibenzoate from which the contaminating antipode was removed by crystallization.
Synthesis and catalytic reactivity of D4-symmetric dinorbornabenzene-derived metallotetraarylporphyrins
Halterman, Ronald L.,Jan, Shyi-Tai,Nimmons, Heather L.,Standlee, David J.,Khan, Masood A.
, p. 11257 - 11276 (2007/10/03)
The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5: 8-dimethanoanthracene-9-carboxyaldehyde, with pyrrole produced the first chiral tetraarylporphyrin 1 exhibiting D4-symmetry. The resolved benzaldehyde was synthesized in seven steps from p-benzoquinone and cyclopentadiene and included a resolution via diastereomeric ketals. A manganese chloride complex of porphyrin 1 was used as a catalyst for the asymmetric epoxidation of aromatic substituted alkenes in the presence of excess sodium hypochlorite in up to 7,200 turnovers and up to 76% e.e and >90% yield.
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.
