- Enantioselective synthesis of (-)-(1R,2R)-1,2-dihydrochrysene-1,2-diol
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A general chiral building block containing the 1R,2R-trans-diol moiety was constructed utilizing the stereoselective Shi-epoxidation reaction on a tetralone scaffold assembled by a Negishi cross-coupling on N,N-diethylbenzamide. Further elaboration of thi
- Lorentzen, Marianne,Sydnes, Magne O.,J?rgensen, K?re B.
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- Synthesis of the Dihydrodiol and Diol Epoxide Metabolites of Chrysene and 5-Methylchrysene
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Carcinogenic polycyclic aromatic hydrocarbons are known to undergo enzymatic activation to diol epoxide metabolites bearing an epoxide ring in a bay molecular region.Introduction of a methyl group into a nonbenzo bay region position generally enhances carcinogenic activity.We now report efficient syntheses of the diasteromeric anti and syn bay region diol epoxide derivatives of both chrysene and 5-methylchrysene (5-MC) in both bay regions.The anti- and syn-1,2-diol-3,4-epoxide derivatives of 5-MC (1b and 2b) are the first examples of synthetic diol epoxides with a methyl group in the same bay region as the epoxide ring.NMR analysis indicates that these diol epoxide derivatives and the related dihydrodiols, with the exception of 2b and the syn-7,8-diol-9,10-epoxide of 5-methylchrysene (2c), exist preferentially in the diequational conformation in solution; 2b and 2c show a slight predominance of the diaxial conformer.All the synthetic diol epoxides were sufficiently stable to conduct biological experiments on tumorigenicity and DNA binding on mouse skin; the results confirm that 1b is the major active carcinogenic form of 5-methylchrysene which binds covalently to DNA in vivo.
- Harvey, Ronald G.,Pataki, John,Lee, Hongmee
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p. 1407 - 1412
(2007/10/02)
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- Synthesis of the Enantiomeric Bay-Region Diol Epoxides of Benzanthracene and Chrysene
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Both trans-3,4-dihydroxy-3,4-dihydrobenzanthracene and trans-1,2-dihydroxy-1,2-dihydrochrysene are known proximate carcinogens of their respective hydrocarbons.The present study describes the synthesis of their (+)- and (-)-enantiomers as well as the d
- Yagi, Haruhiko,Vyas, Kamlesh P.,Tada, Masao,Thakker, Dhiren R.,Jerina, Donald M.
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p. 1110 - 1117
(2007/10/02)
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