Diterpenoid alkaloid natural products comprise over 1,000 members, primarily isolated from the Aconitum and Delphinium genera of plants. Diterpenoid alkaloid natural products possess a variety of biological activities, many resulting from interactions with voltage-gated ion channels, providing opportunities for total synthesis to contribute to the study of ion channels in the brain, as well as further investigating the structure-activity relationships between these alkaloids and ion channels. Furthermore, these diterpenoid alkaloids are complex, caged, often highly oxygenated molecules, making their synthesis a challenging and worthwhile endeavor. A unified approach to the entire family of diterpenoid alkaloid natural products is being investigated from a common bicyclic anhydride precursor, easily accessible through a Diels-Alder reaction. Addition of stabilized benzyl nucleophiles to the cyclic anhydride proceeds with high chemo- and diastereoselectivity to afford products that can be elaborated to construct key motifs in a number of C18, C19, and C20-diterpenoid alkaloids.

Progress toward a unified synthesis of diterpenoid alkaloid natural products

247th National Meeting (2014)

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