Core Modification of Cytisine: A Modular Synthesis

Getting down to the core: A novel, modular, and more robust synthesis of cytisine, a partial agonist selective for the α4β2 nicotinic acetylcholine receptor, also allows modification of the core structure, as exemplified by the first azacytisine and a cytisine–varenicline hybrid. Key steps include S...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-05, Vol.50 (22), p.5162-5165
Main Authors: Hirschhäuser, Christoph, Haseler, Claire A., Gallagher, Timothy
Format: Article
Language:English
Subjects:
acetylcholine receptor
Alkaloids - chemical synthesis
Alkaloids - chemistry
Azocines - chemical synthesis
Azocines - chemistry
Benzazepines - chemistry
Cyclization
cytisine
heterocycles
Nicotinic Agonists - chemical synthesis
Nicotinic Agonists - chemistry
pyridone
Pyridones - chemistry
Quinolizines - chemical synthesis
Quinolizines - chemistry
Quinoxalines - chemistry
Receptors, Nicotinic - chemistry
Receptors, Nicotinic - metabolism
Tin Compounds - chemistry
Varenicline
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Summary:Getting down to the core: A novel, modular, and more robust synthesis of cytisine, a partial agonist selective for the α4β2 nicotinic acetylcholine receptor, also allows modification of the core structure, as exemplified by the first azacytisine and a cytisine–varenicline hybrid. Key steps include Stille coupling of heteroarylstannanes with a bromolactam motif and an in situ epimerization/alkylative cyclization to complete the tricyclic core (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100441