Progress towards the total synthesis of aconitine

ORGN 858

Rosemary M. Conrad, rconrad@stanford.edu and Justin Du Bois, jdubois@stanford.edu. Department of Chemistry, Stanford University, Stanford, CA 94305-5080
Aconitine, isolated from aconite plants, is a persistent activator of voltage-gated sodium channels. Synthetic variants of this family of alkaloids could aid in the study of their biological function. Progress towards the synthesis of the natural product will be described. The highly oxygenated D ring is accessed through a hypervalent iodine oxidation of a vanillin-based arene precursor. Additional significant transformations that will be presented include ring-closing metathesis of a vinyl sulfide and selective methylation of a tetra-ol.