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Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1?-hydroxy-17-veratroyldictyzine, and Paniculamine.

ABSTRACT: The denudatine-type diterpenoid alkaloids cochlearenine, N-ethyl-1?-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.

SUBMITTER: Kou KG

PROVIDER: S-EPMC5076861 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine.

Kou Kevin G M KG Li Beryl X BX Lee Jack C JC Gallego Gary M GM Lebold Terry P TP DiPasquale Antonio G AG Sarpong Richmond R

Journal of the American Chemical Society 20160822 34

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. ...[more]

PMID: 27525345

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