Synthesis of spirocycles through C-H-activation and their application in medicinal chemistry

• Applicant: Dr. Kerstin Hiesinger
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: since 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 490859623

The aim of this project is to synthesize spirocyclic lactones and evaluate them as potential sigma receptor ligands. These target structures are characterized by a generally difficult to access three-dimensional structure. In this project, a novel synthetic method will be developed to build such structures. For this purpose, a palladium-catalyzed cleavage of usually unreactive carbon-hydrogen bonds (C-H activation) will be used to react with carboxylic acids in a regioselective manner. Via olefination and subsequent cyclization, the targeted structures will be built using nitrogen-containing carboxylic acids as reactants, which have not been used in the literature so far. The project includes the development and optimization of suitable catalysts and reaction conditions, as well as the subsequent establishment of a broad substance library for biochemical evaluation.

• DFG Programme: WBP Position