SYNTHESIS, CONFIGURATIONAL ASSIGNMENT, AND CONFORMATIONAL-ANALYSIS OFBETA-HYDROXY SULFOXIDES, BIOISOSTERES OF OXISURAN METABOLITES, AND THEIR O-METHYL DERIVATIVES

Synthesis, configurational assignment, and conformational analysis of diastereoisomers of 2-(methylsulfinyl)-1-(2-quinolyl)ethanol, 3a, 2-(m ethylsulfinyl)-1-(1-isoquinolyl)ethanol, 3b, 2-(methylsulfinyl)-1-(2-p yrazyl)ethanol, 3c, and their O-methyl derivatives 4a-c are reported. The configurational assignment and conformational analysis of the two diastereoisomers of beta-hydroxy sulfoxides and beta-methoxy sulfoxide s have been carried out from the observed vicinal coupling constants u sing the molecular mechanics force field (MMX) and the Altona relation ship as fundamental tools. The conformational equilibrium is explained in terms of polar and steric factors. Of significant importance was t he role of intramolecular hydrogen bonding in the RS/SR isomers of bet a-hydroxy sulfoxides.