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Synthesis of Epibatidine Analogues Having a 2‐Substituted 2‐Azabicyclo[2.2.2]octane Skeleton
Author(s) -
Wauters Iris,
De Blieck Ann,
Muylaert Koen,
Heugebaert Thomas S. A.,
Stevens Christian V.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301397
Subject(s) - epibatidine , chemistry , cyclohexanone , octane , cyanide , propellane , organic chemistry , bicyclic molecule , stereochemistry , combinatorial chemistry , biochemistry , receptor , nicotinic agonist , nicotinic acetylcholine receptor , catalysis
The synthesis of 1‐cyano‐2‐aza‐[2.2.2]bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were fully deprotected to give the potentially active compounds. The highly hydrophilic character of the compounds resulted in a difficult isolation and purification of the epibatidine analogues.