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Synthesis of higher oxidized metabolites of dibenz(a,j)anthracene implicated in the mechanism of carcinogenesis
- Source :
- Journal of Organic Chemistry. Nov 13, 1998, Vol. 63 Issue 23, p8125, 8 p.
- Publication Year :
- 1998
-
Abstract
- The unsymmetrical 3,4,8,9-bis(dihydrodiol) and the 10- and 11-phenolic trans-3,4- dihydrodiols of dibenz(a,j)anthracene were efficiently synthesized. The synthetic approach involves as key steps the asymmetric dihydroxylation of a stilbene precursor using a Sharpless catalyst and intramolecular cyclodehydrobromination catalyzed by Pd(PPh3)2Cl2. Good yields were obtained in all 13 steps of the synthesis of 3,4,8,9-bis(dihydrodiol) except one, with the overall yield placed at 17%.
Details
- ISSN :
- 00223263
- Volume :
- 63
- Issue :
- 23
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.53414358