Syntéza C-organyldeoxyribozidových a C-organylribozidových derivátov s využitím katalýzy komplexov prechodných kovov

Bobula, Tomáš

The aim of my project was to examine reactivity of the triple bonds present in both C- alkynylriboside and C-alkynyldeoxyriboside structures by means of an organocatalysis with the transition metal complexes (Pd, Rh, Ru, Ir, Fe, Ni). I hereby paid attention to the development of an alternative synthetic approach leading to substituted derivatives of alkynylferrocene. The applied synthetic methodologies were based on [2+2+2] cyclotrimerization, Sonogashira cross-coupling reaction and alkyne cross-metathesis. The main targets were C-arylribosides, C-aryl-/C-hetarylalkynyldeoxyribosides and aryl- /alkylethynylferrocenes. My project can be divided into three following sections: The first part was focused on the synthesis of C-arylribosides by [2+2+2] cyclotrimerization. It is powerful reaction where benzene ring is formed in one reaction step from ethynylribofuranose and -diyne. The obtained products represent more stable C-ribosides in comparison to naturally occuring types of pyrimidine nucleosides. The second part of my project was similarly pointed to the C-nucleoside preparation. In this case deoxyribofuranose derivatives were prepared by a modified Sonogashira cross- coupling reaction. The optimization of the reaction conditions enabled to assemble aryl-, hetaryl- and...

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