Imidazole-Analogues of 6-Epicastanospermine and of 3,7a-Diepialexine

The chiral bicyclic imidazol derivatives 7 and 8 were obtained from D-glucose derivative 9 by a sequence of selective protection/deprotection and intramolecular S_N2 reactions. Triols 7 and 8 are analogues of 6-epica-stanospermine ( 4 ) and of 3,7a-diepialexine ( 6 ), respectively, and are potential glycosidase inhibitors. However, their anti-HIV activity proved to be only marginal.