Biomimetic synthesis of brevianamide alkaloids

The brevianamides are a family of fungal derived prenylated indole alkaloids. Their range of complex structures are accompanied by a diverse array of biological activity. The brevianamides were the first reported examples of the wider bicyclo[2.2.2]diazaoctane class of natural products, which have been of continued interest due to their impressive polycyclic structures and the potential role of Diels–Alderase enzymes in their biogenesis. Despite prolonged synthetic attention, several important brevianamides have yet to succumb to total synthesis and many aspects of their biosynthesis remain unclear. This thesis describes our biomimetic synthetic studies towards these complex natural products, which has resulted in several short and efficient total syntheses. These syntheses have been enabled by a substantially improved synthesis of key intermediates, which are of general utility for the wider family of natural products