Application of coupling reaction between lithiated toluamide and benzonitrile for the synthesis of phenolic benzo[c]phenanthridine alkaloid, oxyterihanine.
The total synthesis of the natural phenolic benzo[c]phenanthridine alkaloid, oxyterihanine, was accomplished via substituted 3-arylisoquinoline intermediate. The key reaction was a coupling between the o-toluamide 4 and the benzonitrile 5.
Le Thanh
Nguyen
N
College of Pharmacy, Research Institute of Drug Development, Chonnam National University, Gwangju 500-757, Korea.
Van
Hue Thi My
HT
Lee
Suh-Hee
SH
Choi
Hyun Jin
HJ
Lee
Kwang Youl
KY
Kang
Bok Yun
BY
Cho
Won-Jea
WJ
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001549:Benzamides / Q000737:chemistry*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000737:chemistry*; D010617:Phenanthridines / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D032106:Zanthoxylum / Q000737:chemistry
D000470:Alkaloids; D001549:Benzamides; D007202:Indicators and Reagents; D009570:Nitriles; D010617:Phenanthridines; C527052:oxyterihanine; C014356:benzonitrile