Synthesis of (+/-)-isofagomine and its stereoisomers from arecoline

Authors
Hansen, SU Bols, M
Citation
Su. Hansen et M. Bols, Synthesis of (+/-)-isofagomine and its stereoisomers from arecoline, J CHEM S P1, (6), 2000, pp. 911-915
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
6
Year of publication
2000
Pages
911 - 915
Database
ISI
SICI code
0300-922X(2000):6<911:SO(AIS>2.0.ZU;2-W
Abstract
(+/-)-Isofagomine (1) and all its stereoisomers were prepared in a short sy nthesis from arecoline. The double bond of arecoline was isomerised to be n o 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.