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Updated: Aug 9, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Total synthesis of (+/-)-cytisine
B T O'Neill1, D Yohannes, M W Bundesmann
1Pfizer Global Research and Development, Pfizer Inc., 8220-4111 Groton, Connecticut 06340, USA. brian_t_oneill@groton.pfizer.com
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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