SOLID-PHASE SYNTHESIS OF SMALL ORGANIC-MOLECULES BASED ON THIAZOLIDINE SCAFFOLD

2-Substituted thiazolidine-4-carboxylic acids were obtained by reactio n of aldehydes with unprotected (R)-cysteine attached to the polymeric support via an ester bond. Subsequent transformation into N-acyl deri vatives followed by alkaline hydrolysis provided almost exclusively th e corresponding (2R,4R)-stereoisomer. A convenient solid phase synthes is of substituted thiazolidines, including an evaluation of aldehydes, conditions for N-acylation and S-oxidation as well as the stability o f thiazolidines to reagents used in solid phase synthesis are describe d.