Total syntheses of novel cytocidal beta-carboline alkaloids, oxopropalines D and G.
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.
Choshi
T
T
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Hiroshima, Japan.
Kuwada
T
T
Fukui
M
M
Matsuya
Y
Y
Sugino
E
E
Hibino
S
S
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
D000900:Anti-Bacterial Agents; D002243:Carbolines; D007202:Indicators and Reagents; C085036:oxopropaline D; C085038:oxopropaline G