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Drawing inspiration from the structural features of some natural polyphenols, the synthesis of two different model compounds as potential inhibitors of HIV integrase (IN) has been described. The former was characterised by a diketo acid (DKA) bioisostere, such as a β-hydroxycarbonyl moiety, between two fragments containing aromatic groups, while in the latter an epoxide linked two polyoxygenated aromatic residues. The moieties present in the structures are thought to function by chelating divalent metal ions on the enzyme catalytic site. Overall, 10 compounds were prepared and some of that submitted to molecular modelling studies (to investigate their interactions with the active site of IN), to metal titration studies (to detect their chelating capability) and to biological assays.

The Lewis acid-catalyzed regioselective azidolysis of 2,3-three membered heterocyclic amines has been investigated. The results obtained demonstrated that using TMSN3 as a source of azide, the appropriate choice of Lewis acid allowed to obtain different regio- and stereocontrolled precursors of aminoalcoholic and triaminic sequences. Considering the occurrence of these moieties in the structure of many biologically active compounds, the present methodologies could represent a powerful tool in organic synthesis for the preparation of interesting molecules.

Two conformationally constrained compounds similar to chicoric acid but lacking the catechol and carboxyl groups were prepared. In these analogues, the single bond between the two caffeoyl fragments has been replaced with a chiral oxirane ring and both aromatic residues modified protecting completely or partially the catechol moiety as methyl ether. Preliminary molecular modelling studies carried out on the two analogues showed interactions near the active site of HIV integrase; however, in comparison with raltegravir, the biological evaluation confirmed that CAA-1 and CAA-2 were unable to inhibit infection at lower concentration.

The Lewis acid-catalyzed regioselective azidolysis of 2,3-three membered heterocyclic amines has been investigated. The results obtained demonstrated that using TMSN3 as a source of azide, the appropriate choice of Lewis acid allowed to obtain different regio- and stereocontrolled precursors of aminoalcoholic and triaminic sequences. Considering the occurrence of these moieties in the structure of many biologically active compounds, the present methodologies could represent a powerful tool in organic synthesis for the preparation of interesting molecules.

The title reagent is an efficient nontoxic, biodegradable acetyl source affording the corresponding acetamides in very high yields without any purification.

The first example of the title reaction is presented by using a green and mild methodology.

The umpolung reaction of α,β-unsaturated aldehydes to saturated esters has been carried out in an ionic liquid by organocatalysis of electrogenerated NHC. The roles of solvent, precatalyst and proton donor of the ionic liquid have been verified and good to high yields of esters have been obtained using a “green” and mild methodology.

Isopropenyl acetate was proved to be an efficient reagent for acetylation of amine in the absence of solvent and catalyst. The corresponding acetamides were obtained in very high yields without any purification.

The Lewis acid-catalysed regioselective azidolysis of 2,3-epoxy amines has been investigated. The results obtained demonstrated that using TMSN 3 as a source of azide, the appropriate choice of Lewis acid allowed to direct the regiochemistry of the ring opening. The present methodologies provide a powerful tool in organic synthesis for the preparation of diaminoalcohol moieties.

Scutellarein is a component of Scutellaria, recently known as a potent cytotoxic agent on human leukaemia cells. The aim of this study was the synthesis of scutellarein and its methylated derivative. The new features are the innovating method to afford flavones from flavanones and the A-ring regioselective bromination step that lead to the target molecule by a facile and high-yielding pathway.

A new, simple, and mild regio-and stereocontrolled azidolysis of vinylepoxides with TMSN3/BF3 system is reported. The method appears of general value and works very well particularly in the presence of electron-poor olefins, regardless of the size of substituents on the heterocyclic ring.

A new, simple, and mild regio-and stereocontrolled azidolysis of vinylepoxides with TMSN3/BF3 system is reported. The method appears of general value and works very well particularly in the presence of electron-poor olefins, regardless of the size of substituents on the heterocyclic ring.

The regio- and stereo controlled opening of 2,3-epoxy amines and 2,3-aziridine amines by MgBr2 is studied.