Prenylated indole alkaloids containing the [2.2.2]-diazabicyclic core structure are found in both marine and terrestrial fungal species and several of these complex molecules show promise as insecticidal, anti-inflammatory, and anti-cancer agents. Beginning with 2,5-diketopiperazine starting materials, we have advanced synthetic methods that assemble the [2.2.2]-diazabicyclic function in a domino reaction sequence featuring aldol condensation, alkene isomerization, and hetero-Diels-Alder cycloaddition. Exploration of stereoselective intermolecular Diels-Alder cycloadditions leading to natural products that contain the [2.2.2]-diazabicyclic core will be discussed, including efforts directed toward the synthesis of brevianamide B and stephacidin A.

Stereoselective synthesis of the bicyclo[2.2.2]diazaoctane family

250th National Meeting (2015)

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