title: Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Kevin G M
authors.initials: KG
authors.lastname: Kou
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Beryl X
authors.initials: BX
authors.lastname: Li
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Jack C
authors.initials: JC
authors.lastname: Lee
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Gary M
authors.initials: GM
authors.lastname: Gallego
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Terry P
authors.initials: TP
authors.lastname: Lebold
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Antonio G
authors.initials: AG
authors.lastname: DiPasquale
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D004224:Diterpenes; C034767:denudatine