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Facile synthesis of (±)‐, (+)‐, and (‐)‐galanthamine
Author(s) -
Szewczyk Jerzy,
Wilson Joseph W.,
Lewin Anita H.,
Carroll F. Ivy
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320132
Subject(s) - chemistry , acetylcholinesterase , aluminum hydride , lithium (medication) , alkaloid , acetylcholinesterase inhibitor , stereochemistry , organic chemistry , enzyme , medicine , methoxide , endocrinology , catalysis
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 (1 S )‐camphanate esters and obtained both natural (‐)‐ and unnatural (+)‐galanthamine by lithium aluminum hydride removal of the acyl group.