Synthesis of New Medium- and Large- Sized Racemic and Chiral Lactones

Abstract

Successive reaction of long chain -1, -2, -4 and -5 hydroxycarboxylic acids 1a-1e with a cyanuric chloride (CC) and triethylamine afforded the corresponding racemiclactones 2a-2e in high yields. Optically pure R lactones 4a-4e were synthesizedstereoselectively by porcine pancreas lipase-catalyzed resolution of racemic 2a-2e. Theresolution conditions were investigated, determined and optical rotations were measured. Thementioned chiral lactones were synthesized by this method for the first time. The obtainedracemic and chiral lactones were analyzed by NMR, IR, Mass, optical rotation, and elementalanalysis.