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Cyclisations radicalaires 5-endo-trig et Synthèses d'agents anti-cancéreux.

Abstract : The work presented in this manuscript have initially successfully develop two new methods to achieve 5-endo radical cyclizations and a second time to illustrate the potential of synthetic radical chemistry of xanthates, developed within Laboratory, through its application to the synthesis of biologically active substances. In the first part, different approaches to access to γ-lactams by 5-endo radical cyclization without the use of toxic heavy metals such as tributyltin hydride have been studied. The originality of the two systems is developed in the oxidation of the radical resulting from the cyclization. Thus, unlike reactions induced by tributyltin hydride, various unsaturated γ-lactams can be obtained after deprotonation. Work in the second half allowed the development of numerous analogues duocarmycines, who is the subject of biological tests. These different compounds have been prepared through an efficient and convergent which is to couple a core with alkylating arm sandwiching by forming a hydrazone. Various parties have been synthesized alkylating quickly through the application of the sequence of addition-radical cyclization from xanthate, previously developed in the laboratory. A study was also conducted to try to make changes to these molecules. Finally, we have prepared various arms intercalating several methods. We then coupled the various parties. The molecules synthesized showed promising cytotoxic activities (IC50 ~ 0.5-1.2 microM). This study therefore demonstrates the interest in synthetic radical chemistry of xanthates.
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Delphine Dauge. Cyclisations radicalaires 5-endo-trig et Synthèses d'agents anti-cancéreux.. Chimie. Ecole Polytechnique X, 2005. Français. ⟨pastel-00002296⟩

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