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

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.