Research Projects

Spirocyclic scaffolds have drawn the immense interest of researchers in recent years owing to their ubiquity in natural products and have been reported to exhibit various biological properties. As a result, they hold considerable promise as structural leads in drug discovery programmes. Despite this, significant limitations exist in current synthetic approaches to these important scaffolds, and therefore, there is a very high demand for more efficient and environmentally friendly methods for their synthesis. Ring strain in organic molecules is a powerful driving force that promotes reactivity through strain-release, allowing the facile construction of a myriad of complex and biologically relevant molecules via ring-opening or ring-expansion strategies. The proposed project aims at developing novel strain-enabled Truce-Smiles rearrangements under visible light photocatalysis to rapidly construct medicinally relevant spiro-fused oxindoles. The strategy will be extended to the synthesis of spirobicyclo[1.1.1]pentanes (spiro-BCPs) derivatives, which are of high importance in the pharmaceutical industry and materials chemistry. Furthermore, we plan to develop strain--enabled radical cascades involving ring-expansion followed by Truce-Smiles rearrangement to synthesize highly functionalized spirooxindoles. Due to the different optical and biological properties of enantiomers, the synthesis of enantioenriched chiral motifs has been a very active and significant field of research in organic synthesis for decades. Thus, in the last part of the proposal, we plan to develop an enantioselective synthesis of functionalized spiro-fused oxindoles. The novel methodologies proposed herein not only benefit from the formation of highly functionalized spirocycles but also lay solid foundations for the development of other strain-enabled reactions.

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