Synthesis of pharmacologically active compounds by the enantioselective Heck-Matsuda reaction and novel studies concerning the enantioselective acylation of cyclopentenes and cyclohexene compounds

Abstract

The present proposal is divided into two projects. The first one involves the synthetic application of the enantioselective Heck-Matsuda reaction. More precisely, the application of the key product of the desymmetrization of achiral cyclopent-3-enol in total syntheses of pharmacologically active compounds, such as (+)-indatraline (+)-irindalone and prostaglandin analogues. The second project aims at expanding the type of olefins used in the enantioselective Heck reactions. To this goal in mind, we are proposing the investigation of the enantioselective Heck-Matsuda and oxidative Heck reactions using olefins such as cyclopentene and cyclohexene as substrates aiming at adding synthetic value to these compounds. The reaction conditions will be optimized in order to obtain key arylated products in high yields and enantioselectivities. (AU)