63268-37-1Relevant articles and documents
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 (
Preparation of Enantiomers of (+/-)-trans-7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzopyrene
Iyer, Radhakrishnan P.,Slaga, Thomas J.,Pal, Bimal C.
, p. 275 - 278 (2007/10/02)
(+/-)-trans-7,8-Dihydroxy-7,8-dihydrobenzopyrene (VII), obtained from 7,8,9,10-tetrahydrobenzopyrene-7(8H)-one (I) by modifications and improvements of the reported procedures, has been converted into its di-(-) and (+)-menthoxyacetate derivatives in 82percent yield.The diastereomers have been separated by liquid chromatography on Lichrosorp Si 60 (30μ) column (100 cm x 1 cm dia.) using methylene chloride-ethyl acetate (99.4/0.6, v/v) as eluant.The enantiomers are liberated from the separated diastereomers by methanolysis with catalytic amount of sodium methoxide and converted into the enantiomers of (+/-)-trans-7β,8α-dihydroxy- 9α,10α-epoxy-7,8,9,10-tetrahydrobenzopyrene by m-chloroperbenzoic acid in an overall yield of 30percent.The CD and the UV spectra of the diastereomers and the enantiomers are reported.