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DOI: 10.1039/A606686K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1715-1724

Bacterial dioxygenase-catalysed dihydroxylation and chemical resolution routes to enantiopure cis-dihydrodiols of chrysene

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Derek R. Boyd, Narain D. Sharma, Rajiv Agarwal, Sol M. Resnick, Mark J. Schocken, David T. Gibson, Jane M. Sayer, Haruhiko Yagi and Donald M. Jerina

Abstract

Biotransformation of the environmental pollutant chrysene 1 by resting cells of a mutant strain (B8/36) of the soil bacterium Sphingomonas yanoikuyae produces (+)-cis-3,4-dihydroxy-3,4-dihydrochrysene 4 which has been assigned (3S,4R) absolute configuration by stereochemical correlation with (-)-(3S,4R)-cis-3,4- dihydroxy-1,2,3,4-tetrahydrochrysene 6. Both cis-3,4-diol 6 and cis-1,2-dihydroxy-1,2,3,4- tetrahydrochrysene 12 are obtained in enantiopure form after chromatographic separation of the individual bis(2-methoxy-2-phenyl-2-trifluoromethylacetyl) (bis-MTPA) diastereoisomers of compound 6 and the MTPA diastereoisomers of bromohydrin 19, respectively, followed by hydrolysis. A new general synthetic route to cis-dihydrodiols, from the corresponding cis-tetrahydrodiol cyclic carbonates, is used to obtain both racemic and enantiopure forms of the bay-region diol 4, and the non-bay region diol 5. 1H NMR and CD spectra of the cis- and trans-dihydrodiols of chrysene are described.

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