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A streamlined approach to the tertiary amine-containing core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids is presented. A known carvone derivative is converted into the core structure in only four synthetic operations, and it is well poised for further elaboration. The key enabling methodology is a radical cyclization cascade beginning with addition of a secondary, neutral aminyl radical to the β-position of an enone, followed by trapping with a pendant alkyne.

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Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type <i>Daphniphyllum</i> Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical

Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical