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pubmed-article:17252135pubmed:abstractTextEnantiopure trans-dihydrodiols have been obtained by a chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites, obtained by dioxygenase-catalysed arene cis-dihydroxylation at the 2,3-bond of monosubstituted benzene substrates. This generally applicable, seven-step synthetic route to trans-dihydrodiols involves a regioselective hydrogenation and a Mitsunobu inversion of configuration at C-2, followed by benzylic bromination and dehydrobromination steps. The method has also been extended to the synthesis of both enantiomers of the trans-dihydrodiol derivatives of toluene, through substitution of a vinyl bromine atom of the corresponding trans-dihydrodiol enantiomers derived from bromobenzene. Through incorporation of hydrogenolysis and diMTPA ester diastereoisomer resolution steps into the synthetic route, both trans-dihydrodiol enantiomers of monohalobenzenes were obtained from the cis-dihydrodiols of 4-haloiodobenzenes.lld:pubmed
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pubmed-article:17252135pubmed:year2007lld:pubmed
pubmed-article:17252135pubmed:articleTitleChemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers.lld:pubmed
pubmed-article:17252135pubmed:affiliationSchool of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uklld:pubmed
pubmed-article:17252135pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:17252135pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed