63268-38-2Relevant articles and documents
Enantioselective Synthesis of the (+)-anti-7,8-Dihydrodiol-9,10-epoxide of the Potent Carcinogen Benzopyrene
Huang, Xiaoming,Harris, Thomas M.
, p. 1699 - 1700 (2007/10/02)
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.
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.