A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5
R,6
R,7
R,8
R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-
O-
p-methoxybenzyl-3,4-di-
O-benzyl-
/β-
d-
gluco-6-enopyranoside via (1
R,2
S,3
S,4
R,5
S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent (‘Cp
2Zr’) reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new
-mannosidase inhibitor, (1
R,2
R,3
R,5
R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered.