Research

Thesis title: "Ecologically Benign Total Synthesis of Naturally Occurring C-Glycosidic Compounds and Analogues"

Thesis outline: The aim of this research is to synthesize a series of C-glycosidic compounds, specifically Scleropentasides D, E and F, for detailed biological evaluation and synthesis of analogues for drug development. The choice stems from the fact that the general class of Scleropentasides is known to exhibit a variety of biological activities, however thus far, only antioxidative properties were reported for the three compounds in question. Moreover, a previously established synthetic route to reach Scleropentaside A has not yet been applied to Scleropentasides D, E, F and will therefore serve as the starting point for the synthesis plan. The method will then be extended to include disaccharides and monosaccharides, such as furanoses and glucosamine. Furthermore, the project will explore the synthesis of N- and S-containing heterocyclic dithianes, broadening the scope of the suggested research.

As the organic chemistry places greater and greater emphasis on the greenness of the processes and fulfilling the twelve green chemistry principles, certain solutions explored within this project would aid those efforts. Firstly, an electrocatalytic Ullmann-type reaction will be attempted as an alternative for C-H arylation using a stoichiometric amount of heavy metals. Secondly, the project will involve attempting a light-mediated stereoselective glycosylation reaction allowing a greener access to Scleropentaside analogues.

Supervisor: Nina Schützenmeister

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