Over the last 40 years, much work has been achieved for the conception of macrocycles in order to access to new biologically active compounds. In this context, we investigated the reduction of carbonyl functions from diketal dilactams to access both 6 diketal amino-lactams and cyclams homologues of 6 diketal diamines. Diketal dilactams were produced from hydroxyamidoketals, which are obtained from corresponding β-aminoalcools. We have shown that the efficiency of the reduction was dependent on both the nature of the substituant and the stereochemistry of the ketal OMe group. Diketal amino-lactames were obtained at low concentrations in diketal dilactams (3 to 14 × 10-3 M) whereas diketal diamines were obtained at high concentrations (15 to 30 × 10-3 M). Among the different molecules synthetised, diketal diamines led to the maximum complexation rate of 18% with technetium radioelement-99m (99mTc). We also optimised a new route for the synthesis of dimeric compounds; 5 bis-diketal amino-lactames and 2 bis-diketal diamines were isolated. These latter compounds are homologues of bicyclams which display anti-viral activity.
