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The University of Southampton

Research project: Harrowven: Total Synthesis of Toddaquinoline

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Our work in on the addition of radical intermediates to arenes and aromatic heterocycles all stemmed from our realisation of the first total synthesis of toddaquinoline, which used a radical cyclisation to a pyridine as a key step.

Intriguingly, cyclisation gave a mixture of regioisomeric products when mediated with tributyltin hydride but proceeded in a regioselective manner when using cobalt(I). We presume that the cobalt(II) intermediate produced on single electron transfer, forms a Lewis acid – Lewis base complex with the pyridine to bias addition of the nucleophilic radical intermediate to C2.

Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow
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