Scaffolded bis-azasugars: A dual warhead approach to glycosidase inhibition

Article abstract of DOI:10.1016/S0040-4039(97)10616-5

Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadienediol 6 and α,ω-diborane coupling partners derived from the hydroboration of the corresponding diene. Ozonolysis and selective reduction protocols served to provide selectively the α/α or β/β tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C₈ linked DMJ analogue 1 showed inhibitory activity against glycosidase enzymes.