Total synthesis of (+/-)-cytisine.
[reaction:see text] The nicotine partial agonist cytisine was prepared in five steps featuring an "in situ" Stille or Suzuki biaryl pyridine coupling. Differentiation of the pyridyl rings was accomplished via selective benzylation and then reduction of a pyridinium ring. The penultimate diazabicyclo[3.3.1]nonane intermediate was obtained with high diastereoselectivity. A similar sequence has been employed for the synthesis of novel derivative 9-methoxycytisine.
O'Neill
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BT
Pfizer Global Research and Development, Pfizer Inc., 8220-4111 Groton, Connecticut 06340, USA. brian_t_oneill@groton.pfizer.com
Yohannes
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D
Bundesmann
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Arnold
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EP
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001392:Azocines; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018722:Nicotinic Agonists / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D001392:Azocines; D018722:Nicotinic Agonists; D011807:Quinolizines; C004712:cytisine; D000093843:Quinolizidine Alkaloids