Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, <i>N</i>‑Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine

The denudatine-type diterpenoid alkaloids cochlearenine, N-ethyl-1α-hydroxy-17-veratroyldictyzine, and paniculamine have been synthesized for the first time (25, 26, and 26 steps from 16, respectively). These syntheses take advantage of a common intermediate (8) that we have previously employed in preparing aconitine-type natural products. The syntheses reported herein complete the realization of a unified strategy for the preparation of C20, C19, and C18 diterpenoid alkaloids.