Assembling of polyaryl based unnatural amino acid derivatives and modification of fluorene and fluorenone scaffolds via C-H functionalization

Abstract

Amino acids are fundamental and vital class of bioactive molecules of life, and they play several significant roles in living systems. Amino acid derivatives are privileged molecules and versatile building blocks in organic synthesis and drug discovery research. Especially, the non proteinogenic or unnatural amino acid derivatives have found substantial importance as synthetic building blocks and pharmacologically active motifs. Various unnatural amino acid-derived peptide mimetics have been found to possess enhanced biological activities and proteolytic resistance and hence are considered as potential drug candidates. Given their incredible importance numerous synthetic methods are employed for synthesizing unnatural amino acids. The bidentate directing-group-aided C-H bond functionalization is also well-established method for synthesizing unnatural amino acid derivatives. Biaryls skeletons are significant because of their existence in biologically active molecules, natural products and functional materials. Biphenyl skeleton possessing fluorene and fluorenone scaffolds are tricyclic aromatic compounds with enhanced π conjugation and a rigid plane. Since, polyaryl based systems have extended π-conjugation and exhibit applications in biological and materials sciences. This thesis manifests the assembling of polyaryl based unnatural amino acids and modified fluorene and fluorenone scaffolds via C-H functionalization.