Smyrnov O. Synthesis of functionalized derivatives of tricyclo[3.3.0.03,7]octane and its analogues.

The work is devoted to the development of methods for the synthesis of tricyclo[3.3.0.03,7]octane derivatives, the study of mechanistic aspects of the formation of this structural element, as well as the study of the possibilities of functionalization of the obtained compounds. The main synthetic result of the research carried out as part of the dissertation work was the development of multigram preparative methods for the synthesis of the main building blocks and fundamental research of the key stage - cyclization with the formation of tricyclo[3.3.0.03,7]octane structural element (bisnoradamantane) and tricyclo[3.3.1.02,7]nonane (noradamantan). Using the approaches known in the literature, the synthesis of tricyclo[3.3.0.03,7]octane-1,5-dicarboxylate was successfully carried out - a key intermediate for further research. A more in-depth study was also conducted to study the dependence of the formation of two different tricyclic compounds (tricyclo[3.3.0.03,7]octane and tricyclo[3.3.1.02,7]nonane) on the mutual location of two stereocenters in the starting compound for the cyclization reaction. To carry out this part of the study, three possible diastereomers of Dimethyl(2s,3as,5s,6as)-octahydropentalene-2,5-dicarboxylate (exo, exo-, endo, exo-, endo, endo-isomers, respectively) were synthesized and their reaction ability was studied under the conditions of the cyclization reaction.