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Total Synthesis of (±)-Cytisine
Journal article   Peer reviewed

Total Synthesis of (±)-Cytisine

Brian T O'Neill, Daniel Yohannes, Mark W Bundesmann and Eric P Arnold
Organic letters, Vol.2(26), pp.4201-4204
12/01/2000
DOI: 10.1021/ol0067538
PMID: 11150199

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Abstract

[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.

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