Formation of an unusual dimeric compound by lead tetraacetate oxidation of a corynanthe-type indole alkaloid, mitragynine.
Lead tetraacetate oxidation of a Corynanthe-type indole alkaloid, mitragynine, produced mainly 7-acetoxyindolenine derivative (2) together with a dimeric compound (4) as a minor product. The novel structure having a bridge between the C-11' and C-7 positions in the respective indolenine parts and its formation mechanism were studied.
Takayama
Hiromitsu
H
Graduate School of Pharmaceutical Sciences, Chiba University, Japan. htakayam@p.chiba-u.ac.jp
Ishikawa
Hayato
H
Kitajima
Mariko
M
Aimi
Norio
N
D000840:Anisoles; D002855:Chromatography, Thin Layer; D019281:Dimerization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D000840:Anisoles; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D046948:Secologanin Tryptamine Alkaloids; C031201:1,3-dimethoxybenzene; C029433:lead tetraacetate; C001801:mitragynine