The enantioselective total synthesis of a beta-carboline alkaloid, (S)-(-)-dichotomine C.
The first enantioselective synthesis of a beta-carboline alkaloid, dichotomine C, possessing antiallergic effects, was achieved by constructing a beta-carboline framework based on the microwave-assisted thermal electrocyclic reaction of a 1-azahexatriene system, followed by the Sharpless asymmetric dihydroxylation.
Omura
Kana
K
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima, Japan.
Choshi
Tominari
T
Watanabe
Shiroh
S
Satoh
Yuhsuke
Y
Nobuhiro
Junko
J
Hibino
Satoshi
S
D018926:Anti-Allergic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002243:Carbolines / Q000138:chemical synthesis* / Q000302:isolation & purification; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003500:Cyclization; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008872:Microwaves; D013237:Stereoisomerism
D018926:Anti-Allergic Agents; D002243:Carbolines; D007202:Indicators and Reagents; C527322:dichotomine C