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A number of conceptually new synthetic approaches to the elaboration of constitutionally diverse isoindolinones have been disclosed. The main objective was to develop synthetic tactics for the creation of the lactam unit that would allow for incorporation of appropriate functionalities liable to give access to an array of synthetic, natural and/or bioactive compounds through rather simple chemical manipulation. The flexibility and potentiality of these new processes have been further exemplified by the total synthesis of exemplary representatives in both series, i.e. alkaloids and compounds endowed with chemotherapeutic properties.