Synthesis of spirocycles through C-H-activation and their application in medicinal chemistry
Final Report Abstract
As part of this project, spirocyclic compounds were synthesized using the modern C–H activation reaction. Spirocycles are ring systems connected via one carbon atom. These spirocycles are to be tested as modulators of σ-receptors. σ-receptors are involved in several diseases such as Alzheimer's, cancer and neuropathic pain. The C–H olefination for the synthesis of the lactones was successfully established after several optimization studies and the yield of the test system was 73%. The isolation of the target compound required an optimized purification protocol and the further reaction turned out to be complex, as standard protocols for benzylation gave only moderate yields of the target compound. A suitable protocol was established and a compound was successfully isolated. The potential to modulate σ-receptors will be investigated after the synthesis of further derivatives.
Publications
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Preparative Scale Applications of C−H Activation in Medicinal Chemistry. Angewandte Chemie International Edition, 62(45).
de Jesus, Rita; Hiesinger, Kerstin & van, Gemmeren Manuel
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Pd-catalysed direct β-C(sp3)–H fluorination of aliphatic carboxylic acids. Nature Synthesis, 3(10), 1292-1298.
Mal, Sourjya; Jurk, Friedrich; Hiesinger, Kerstin & van, Gemmeren Manuel
