Journal of Medicinal Chemistry p. 1091 - 1094 (1982)
Update date:2022-08-06
Topics:
Cannon, Joseph G.
Crockatt, Dale M.
Long, John Paul
Maixner, William
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-β-methylcholine.
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