Six-step synthesis of (S)-brevicolline from (S)-nicotine.
[reaction: see text] A six-step synthesis of (S)-brevicolline from (S)-nicotine is reported. Regioselective trisubstitution of the pyridine ring of nicotine, followed by successive Suzuki cross-coupling and Buchwald amination reactions, afforded the enantiopure beta-carboline alkaloid, brevicolline.
Wagner
Florence F
FF
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Comins
Daniel L
DL
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D031255:Carex Plant / Q000737:chemistry; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D009538:Nicotine / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D002243:Carbolines; D007211:Indoles; C519984:brevicolline; C010688:brevicarine; D009538:Nicotine