Diterpenoid alkaloids are a family of over 1000 natural products isolated from several genera of plants including Aconitum, Delphinium, and Consolida. While many of these natural products can be grouped into large families with similar structures, arcutine and its related compounds comprise a group of only 3 members, all possessing a highly unusual [5.3.3.0.0]tridecane core. In addition to their unique architecture, we became interested in these compounds due to their unexplored biological activity. Many diterpenoid alkaloids have been shown interact with voltage gated sodium channels, which modulate a number of important biological functions. The biosynthesis of this unique scaffold has also garnered our interest and we plan to explore the relationship between arcutine and the other more prevalent diterpenoid families. Herein we report our progress toward the synthesis of these natural products using a Diels-Alder based approach to form two of the vicinal quaternary centers in this highly caged polycyclic structure. After a series of elaboration steps a second Diels-Alder reaction is expected to furnish the completed core, which can then be functionalized to complete arcutine and the related compounds arcutinine and atropurpuran. Upon completion, the biological activity and biosynthesis of these compounds will be explored.

Toward the total synthesis of the arcutine family of diterpenoid alkaloids

251st National Meeting (2016)

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