SYNTHESIS OF 5-EPI-ISOFAGOMINE VIA ASYMMETRIC CHELATE-ENOLATE CLAISENREARRANGEMENT

Polyhydroxylated piperidines are an interesting class of glycosidase i nhibitors. Chelate enolate Claisen rearrangement of N-protected chiral amino acid eaters gives rise to gamma,delta-unsaturated amino acids, which can be converted to this type of alkaloids. The potential glycos idase inhibitor 5-epi-isofagomine (5) was synthesized by this approach in a highly stereoselective fashion.