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Core Modification of Cytisine: A Modular Synthesis
Author(s) -
Hirschhäuser Christoph,
Haseler Claire A.,
Gallagher Timothy
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100441
Subject(s) - cytisine , chemistry , stille reaction , nicotinic agonist , stereochemistry , combinatorial chemistry , receptor , organic chemistry , polymer , biochemistry
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).