title: Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine-Q.
abstract: The total syntheses of four fawcettimine-related Lycopodium alkaloids, (±)-fawcettimine, (±)-fawcettidine, (±)-lycoposerramine-Q, and (±)-lycoflexine, were completed in a highly stereoselective manner. The Pauson-Khand reaction of 4-methylidene-6-siloxyoct-1-en-7-yne followed by regio- and stereoselective hydrogenation led to the short-step preparation of the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry. The subsequent chemical manipulation of the bicyclic compound afforded the 6-5-9-membered tricyclic dioxo compound, which was then transformed into the four targeted alkaloids in an alternative and more efficient fashion.
authors: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
authors: Naoya
authors: N
authors: Itoh
authors: Takashi
authors: T
authors: Iwata
authors: Hiromi
authors: H
authors: Sugihara
authors: Fuyuhiko
authors: F
authors: Inagaki
authors: Chisato
authors: C
authors: Mukai
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D032502:Lycopodium / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; C524731:fawcettimine; C555161:lycoflexine; C587313:lycoposerramine-Q