Faurine and O-methylfaurine, two novel benzyl-aporphine dimers from Thalictrum fauriei.
Two new benzyl-aporphine dimers, faurine (1) and its O-methyl ether (2), were obtained from Thalictrum fauriei and their structures determined by spectral and chemical methods. Faurine (1), the first dimer with the diphenyl ether connection at C-1 of the aporphine, did not undergo a Hofmann degradation, yet formed a chiral phenanthrene product (6) with cyanogen bromide. Two nondimeric chiral aporphine alkaloids, O-acetylisocorydine and O-methylisocorydine, gave the corresponding phenanthrene products 7 and 8, respectively, under the same conditions, but only compound 7 was optically active.
Lee
S S
SS
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus 43210-1291, USA.
Doskotch
R W
RW
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification*; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification*; D019905:Benzyl Alcohol; D001592:Benzyl Alcohols / Q000737:chemistry; D002850:Chromatography, Gel; D003488:Cyanogen Bromide / Q000737:chemistry; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D010616:Phenanthrenes / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000975:Antioxidants; D001060:Aporphines; D001592:Benzyl Alcohols; D016859:Lipoxygenase Inhibitors; C102969:O-methylfaurine; D010616:Phenanthrenes; C102968:faurine; C081279:aporphine; C030168:isocorydine; C031181:phenanthrene; D019905:Benzyl Alcohol; D003488:Cyanogen Bromide