Dearomatizzazioni mediate da arenofilo verso la sintesi di aminociclitoli e aminoglicosidi

Aminocyclitols and aminoglycosides are important biologically active molecules. Since their discovery they have offered precious help in human medicine, and it is important to find new ways for isolating new compounds that can potentially be of clinical interest. A lot of effort has been made during the years to develop new synthetic pathways to such important targets. This work presents steps that have been made towards such final goal, especially by using new dearomatization strategies that have been developed in the last decade. Thanks to MTAD ability as arenophile to perform photo-induced cycloadditions with various aromatic compounds, new synthetic opportunities have opened. We think that such novel approach could be of great utility for drug discovery. In order to achieve this, screening conditions for developing a 1,4-hydroamination methodology were tried with various palladium sources and hydride sources both on benzene and naphthalene. Moreover, 1,2-hydroaminated and 1,2-carboaminated products were further derivatized towards complex cyclic compounds by using well-established olefin chemistry. Lastly, the search for an adequate protecting group of the acidic urazole moiety was performed, involving a series of electrophiles and conditions.