Concise synthesis of (+/-)-cytisine via lithiation of N-Boc-bispidine.
[reaction: see text] (+/-)-Cytisine has been synthesized in 19% overall yield via a six-step approach from commercially available materials. Key features of this new strategy are as follows: (i) initial construction of the bispidine core, (ii) lithiation-transmetalation-allylation of an N-Boc-bispidine, and (iii) a Pd/C-mediated dihydropyridone oxidation-N-debenzylation process.
Stead
Darren
D
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
O'Brien
Peter
P
Sanderson
Adam J
AJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D001392:Azocines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D008094:Lithium; D011807:Quinolizines; C495809:bispidine; C004712:cytisine; D000093843:Quinolizidine Alkaloids