(+/-)-cis-2-acetoxycyclobutyltrimethylammonium iodide: a semirigid analogue of acetylcholine.
The title compound was prepared to complete a series of small ring (cyclopropane, cyclobutane) cis/trans 1,2-disubstituted semirigid congeners of acetylcholine. A multistep synthetic sequence, beginning with cis-cyclobutane-1,2-dicarboxylic anhydride, permitted unequivocal preparation of the (+/-)-cis target compound 4. The geometry of 4 was confirmed by comparison with an authentic sample of the (+/-)-trans isomer. The cis and trans isomers were equipotent as muscarinic agonists, but they were much weaker than acetyl-beta-methylcholine.
Cannon, JG; Crockatt, DM; Long, JP; Maixner, W
Volume / Issue
Start / End Page
Pubmed Central ID
International Standard Serial Number (ISSN)
Digital Object Identifier (DOI)