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Total Synthesis of (±)-Cytisine

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journal contribution
posted on 07.12.2000, 00:00 by Brian T. O'Neill, Daniel Yohannes, Mark W. Bundesmann, Eric P. Arnold
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.