Facile synthesis of (±)‐, (+)‐, and (‐)‐galanthamine | Zendy

Szewczyk Jerzy | Zendy; Wilson Joseph W. | Zendy; Lewin Anita H. | Zendy; Carroll F. Ivy | Zendy

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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.

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