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

Abstract

Successive reaction of long chain w-1, w-2, w-4 and w-5 hydroxycarboxylic acids 1a-1e with a cyanuric chloride (CC) and triethylamine afforded the corresponding racemic lactones 2a-2e in high yields. Optically pure R lactones 4a-4e were synthesized stereoselectively by porcine pancreas lipase-catalysed resolution of racemic 2a-2e. The resolution conditions were investigated, determined and optical rotations were measured. The mentioned chiral lactones were synthesized by this method for the first time. The obtained racemic and chiral lactones were analysed by NMR, IR, Mass, optical rotation and C,H analysis.