63268-35-9Relevant articles and documents
Enantioselective synthesis of the tumorigenic anti-diol epoxide metabolites of benzo[a]pyrene
Harvey, Ronald G.
, p. 2737 - 2740 (1995)
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 (
Improved Formal Preparation of Enantiomerically Pure anti-Benzopyrene Diol Epoxide.
Negrete, George R.,Meehan, Thomas
, p. 4727 - 4730 (2007/10/02)
We report an improved, economical formal route to enantiomerically pure anti-benzopyrene diol epoxide (BPDE).A trimethylaluminum catalyzed regio- and stereoselective opening of racemic 7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene with Mosher's acid delivers benzylic esters exclusively.This step is a significant improvement over the lack of regioselectivity of standard procedures.We also show that modification of the subsequent chemical steps further shortens the preparation of enantiomerically pure anti-BPDE.