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A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids.

ABSTRACT: 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-1?-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.

SUBMITTER: Kou KGM

PROVIDER: S-EPMC6372304 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids.

Kou Kevin G M KGM Kulyk Svitlana S Marth Christopher J CJ Lee Jack C JC Doering Nicolle A NA Li Beryl X BX Gallego Gary M GM Lebold Terry P TP Sarpong Richmond R

Journal of the American Chemical Society 20170920 39

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 C ...[more]

PMID: 28858498

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