Abstract

Allene towards efficiency: Two new rings, six stereocentres and four CC bonds are generated in synthetically useful yields by double dehydro-Diels–Alder reactions of readily available 1,5-dien-3-ynes and alkenic dienophiles. Computational studies support a mechanism for this often highly stereoselective process involving two concerted cycloaddition events and a 1,2-cyclohexadiene intermediate (see scheme).

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