Total synthesis of (+/-)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides.
[reaction:see text] A synthesis of racemic cytisine 1 has been developed utilizing an intramolecular Heck cyclization to prepare the bridged tricyclic intermediate 2. The cyclization employs activated glutarimide-derived ketene aminals 3 (X = P(O)OEt(2) or SO(2)CF(3)) and represents the first use of such intermediates in metal-catalyzed processes.
Coe
J W
JW
Pfizer Global Research and Development, Pfizer Inc., Groton, Connecticut 06340, USA. coejw@groton.pfizer.com
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D001392:Azocines; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011807:Quinolizines; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D000577:Amides; D001392:Azocines; D011807:Quinolizines; C004712:cytisine; D000093843:Quinolizidine Alkaloids