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This thesis is focused on the study of the central role of chirality in different kind of molecular structures; in particular, new synthetic pathways have been developed to improve the synthesis of already existing drugs, exploring at the same time the relationship between the chirality and the pharmacological properties of these compounds. Moreover, new enantiomeric systems have been synthetized and their pharmacological properties will be tested to verify the potential bioactivity and use as drugs. The thesis is organized in three major sections focusing on the different molecule typology investigated (nucleosides, iminosugars, alkaloids). The studies on nucleosides and iminosugars have been carried out at the department of Chemical Sciences of University of Naples “Federico II”, while the synthesis of alkaloids has been accomplished at the department of Organic Chemistry of the Faculty of Pharmacy of the University of Barcelona.

This thesis is focused on the study of the central role of chirality in different kind of molecular structures; in particular, new synthetic pathways have been developed to improve the synthesis of already existing drugs, exploring at the same time the relationship between the chirality and the pharmacological properties of these compounds. Moreover, new enantiomeric systems have been synthetized and their pharmacological properties will be tested to verify the potential bioactivity and use as drugs. The thesis is organized in three major sections focusing on the different molecule typology investigated (nucleosides, iminosugars, alkaloids). The studies on nucleosides and iminosugars have been carried out at the department of Chemical Sciences of University of Naples “Federico II”, while the synthesis of alkaloids has been accomplished at the department of Organic Chemistry of the Faculty of Pharmacy of the University of Barcelona.