SCAFFOLDED BIS-AZASUGARS - A DUAL WARHEAD APPROACH TO GLYCOSIDASE INHIBITION

Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadie nediol 6 and alpha,omega-diborane coupling partners derived from the h ydroboration of the corresponding diene. Ozonolysis and selective redu ction protocols served to provide selectively the aia or pip tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C-8 link ed DMJ analogue 1 showed inhibitory activity against glycosidase enzym es. (C) 1998 Elsevier Science Ltd. All rights reserved.