This PhD thesis was focused on the study of cascade reactions and allowed the access to a large variety of polycyclic compounds. The extension of several methods employing palladocatalyzed cascade reactions and their limits have been studied. Those cascades are initiated by a 4-exo-dig cyclocarbopalladation, followed by a Sonogashira coupling. With an adequate substrate and the appropriate conditions, the cascade reaction can even be extended by an alcynilation, followed by an eight p electron electrocyclization and a six p electron electrocyclization. Complex scaffolds are thus obtained in only a few steps: fenestradienes and cyclooctatrienes. Derivatives with various substituents in different positions have been synthesized, particularly with heteroatoms. Their access has been ensured by either linear synthesis or a platform approach. This project was completed by an in silico study of the scaffolds regarding their drug-like potential.
