Issue 6, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of (±)-isofagomine and its stereoisomers from arecoline

Steen Uldall Hansena  and  Mikael Bols*a  

* Corresponding authors

a Department of Chemistry, Aarhus University, Langelandsgade 140, Aarhus, Denmark
E-mail: mb@kemi.aau.dk
Fax: +45 86 19 61 99
Tel: +45 89 42 39 64

Abstract

(±)-Isofagomine (1) and all its stereoisomers were prepared in a short synthesis from arecoline. The double bond of arecoline was isomerised to be no longer conjugated to the carboxy, and the ester reduced to (hydroxymethyl)tetrahydropyridine 5 which after dihydroxylation of the alkene, separation and N-demethylation gave 1 and its isomers.

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Article information

DOI
https://doi.org/10.1039/A909472E
Article type
Paper
Submitted
26 Nov 1999
Accepted
23 Jan 2000
First published
24 Feb 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 911-915

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Synthesis of (±)-isofagomine and its stereoisomers from arecoline

S. U. Hansen and M. Bols, J. Chem. Soc., Perkin Trans. 1, 2000, 911 DOI: 10.1039/A909472E

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