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The University of Southampton

Research project: Harrowven: Chemistry Without Reagents

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The ‘reagent free’ cascade sequence employed as a key step in our total syntheses of colombiasin A and elisapterosin B prompted us examine the thermochemistry of cyclobutenones in detail.

These studies led to the discovery of four new thermal rearrangement pathways and a domino reaction leading to quinones, with the new transformations providing rapid access to a diverse array of spirocyclic and polycyclic ring systems in good yield.

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Scheme. New thermally induced rearrangements of cyclobutenones.

We have recently uncovered two further thermal rearrangements of cyclobutenones (unpublished) and are seeking to apply one in a second generation total synthesis of colombiasin A.

Related research groups

Organic Chemistry: Synthesis, Catalysis and Flow
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