Concise synthesis of Cannabisin G.
Cannabisin G (1), a naturally occurring lignanamide, was synthesized in 45% overall yield starting from 3-tert-butyl ethyl ferulate (6). An oxidative coupling by potassium ferricyanide in an alkaline media serves as the key step to construct the biphenylbutadiene skeleton of 1 with high regioselectivity.
Li
Dawei
D
Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, PR China.
Li
Wenling
W
Wang
Qian
Q
Yang
Zhaoqi
Z
Hou
Zijie
Z
D005295:Ferrocyanides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization
D005295:Ferrocyanides; D010636:Phenols; C093865:cannabisin G; C031835:potassium ferrocyanide