Sixth International Conference on Advances in Applied Science and Environmental Technology - ASET 2017
Author(s) : RYSZARD OSTASZEWSKI
Chiral, β,γ-Unsaturated carboxylic acids derivatives are important intermediates in the synthesis of many biologically active compounds; for example anti-microtubule agents , Bisnorvernolepin  and Vineomycinone B2 . Recently we have performed studies on enzymatic kinetic resolution based on esterification of carboxylic acids with orthoestres, used as a donor of alkoxy group [4,5]. As a compound for our studies, we choose 2-benzyl-2-methylbut-3-enic acid, which contains stereogenic quaternary carbon center. This compound is a substrate for the synthesis of irreversible inhibitors of a carboxypeptidase A, a representative zinc-containing proteolytic enzyme . 2-Benzyl-2-methylbut-3-enic acid was synthesized in 4-step synthesis, containing enzymatic hydrolysis of benzylmethylmalonic dimethylester . We propose short, two step synthesis of optically active 2-benzyl-2-methylbut-3-enic acid from commercially available tiglic acid. The results of optimization of the kinetic resolution of 2-benzyl-2-methylbut-3-enic acid, containing enzyme screening, influence of solvent and reaction conditions will be demonstrated..