Absolute configurations of the arene oxide, trans-dihydrodiol and cis-dihydeodiol products resulting from metabolism of quinoline at the 5,6-bond

Autor:	R. Austin S. McMordie, Wayne Levin, Donald M. Jerina, R. Jeremy H. Davies, John F. Malone, Daniel R. Bushman, Michael R.J. Dorriy, Lynne Hamilton, Derek R. Boyd, John J. McCullough, H. Patricia Porter
Rok vydání:	1991
Předmět:	Stereochemistry Organic Chemistry Quinoline Diol Absolute configuration Oxide Diastereomer Epoxide Biochemistry chemistry.chemical_compound chemistry Drug Discovery Hydrolase Enantiomer
Zdroj:	Tetrahedron Letters. 32:2963-2966
ISSN:	0040-4039
DOI:	10.1016/0040-4039(91)80663-q
Popis:	Trans -6-bromo-5-hydroxy-5,6,7,8-tetrahydroquinoline enantiomers have been resolved via their dibenzoyltartrate salt diastereoisomers. X-ray crystallographic analysis of the (+)-dibenzoyltartrate salt obtained from reaction of (+)-dibenzoyltartaric acid and (−)-trans-6-bromo-5-hydroxy-5,6,7,8-tetrahydro-quinoline, when allied to a stereochemical correlation sequence linking the arene oxide, trans -dihydrodiol and cis -dihydrodiol enantiomers, provides an unequivocal assignment of absolute configuration for these quinoline metabolites.
Databáze:	OpenAIRE
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