Facile Synthesis of (¤)-, (+)-, and (-)-Galanthamine
Szewczyk, J., Wilson, J. W., Lewin, A., & Carroll, F. (1995). Facile Synthesis of (¤)-, (+)-, and (-)-Galanthamine. Journal of Heterocyclic Chemistry, 32(1), 195-199. DOI: 10.1002/jhet.5570320132
The Amarylidacea alkaloid galanthamine (1a) is an acetylcholinesterase inhibitor that has been evaluated as a potential agent for the treatment of Alzheimer's disease. We report a very efficent synthesis of (±)-galanthamine [(±)-1a] from readily available isovanillin and tyramine. We have separated racemic galanthamine into its diastereoisomeric (1S)-camphanate esters and obtained both natural (-)- and unnatural (+)-galanthamine by lithium aluminum hydride removal of the acyl group.