SYNTHESIS AND CONFORMATIONAL ANALYSIS OF SOME OXISURAN METABOLITES AND THEIR O-METHYLDERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)90316-3

The synthesis is given of oxisuran (methylsulphinylmethyl-2-pyridyl ketone) and its metabolites and derivatives, whose structures are 2-Py-CO-CH2-SOxCH3 (X=0, 1, 2) and 2-Py-CHOR-CH2SOnCH3 (R=H, Me; n=0, 1, 2).From the results obtained in the reaction of oxisuran with different reducing agents, a new stereochemical pathway is suggested to explain the stereoselectivity observed in the reduction of β-ketosulphoxides with DIBAL.The conformational analysis of hydroxy and methoxyderivates is discussed in relation with that previously reported for 2-thioderivatives of phenylethanol and their O-methylderivates.The configurational assignment of diastereoisomeric sulphoxides is made on the basis of their different conformational behaviour, confirming the assigment deduced from the stereoselectivity observed in the reduction of oxisuran.