title: Total syntheses of novel cytocidal beta-carboline alkaloids, oxopropalines D and G.
abstract: A new type of beta-carboline nucleus, N-methoxymethyl-4-methyl-beta-carboline (4) was synthesized by thermal electrocyclic reaction of a 1-azahexatriene system, involving the indole 2,3-bond. The key compound N-methoxymethyl-1-methoxycarbonyl-4-methyl-beta-carboline (2) was then prepared in a four-step sequence. The total synthesis of oxopropaline G (1e) was achieved from this key compound in four steps. Furthermore, the enantioselective total syntheses of (+)-oxopropaline D (1c) and its enantiomer were also achieved by application of the Sharpless oxidation-procedure in nine steps from 2.
authors.affiliation: Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Hiroshima, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Choshi
authors.forename: T
authors.initials: T
authors.lastname: Kuwada
authors.forename: M
authors.initials: M
authors.lastname: Fukui
authors.forename: Y
authors.initials: Y
authors.lastname: Matsuya
authors.forename: E
authors.initials: E
authors.lastname: Sugino
authors.forename: S
authors.initials: S
authors.lastname: Hibino
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002243:Carbolines / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D002243:Carbolines; D007202:Indicators and Reagents; C085036:oxopropaline D; C085038:oxopropaline G