American Chemical Society
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A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids

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posted on 2017-08-31, 00:00 authored by Kevin G. M. Kou, Svitlana Kulyk, Christopher J. Marth, Jack C. Lee, Nicolle A. Doering, Beryl X. Li, Gary M. Gallego, Terry P. Lebold, Richmond Sarpong
The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18, C19, and C20 families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.