An Investigation into the Synthesis of Some Molecules Related to Methyl Acarviosin

Methyl acarviosin is an impressive inhibitor of some glycoside hydrolases that process substrates containing alpha-D-glucosidic linkages. In an attempt to provide putative inhibitors for enzymes that process beta-D-glucosidic linkages, we report an improved synthesis of a hydroxylated 'methyl beta-acarviosin' and our efforts towards various deoxygenated versions of methyl beta-acarviosin. As well, the synthesis of a 1,3-linked variant of methyl beta-acarviosin is reported, together with an unsuccessful 'tether' approach to construct the crucial nitrogen linkage in the acarviosins.