Isoxazole to oxazole: a mild and unexpected transformation.

3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.

Rapid assembly of highly-functionalised difluorinated cyclooctenones via ring-closing metathesis.

Building block methodology from trifluoroethanol and ring-closing metathesis using a Fürstner modification of Grubbs' conditions allows the rapid synthesis of novel difluorinated cyclooctenones.