An efficient and highly stereoselective synthesis of bicyclic iminosugars, derivatives of polyhydroxylated decahydropyrido[1,2-a]azepine, was developed. Starting from a two-component coupling reaction, through nitrone formation and a 1,3 dipolar cycloaddition, an azabicyclic intermediate was obtained. In subsequent reaction sequences, the azabicyclic intermediate was converted into the corresponding epoxide derivative. The N–O bond reductive cleavage, followed by an intramolecular 7-endo-tet cyclization, was the crucial step leading to seven-membered ring closure. Additionally, an alternative synthetic pathway using the bicyclic iodide derivative was explored. The inhibitory activity of the synthesized decahydropyrido[1,2-a]azepines against selected glycosidases was examined.

开发了一种高效，高度立体选择性的合成双环亚氨基糖的方法，该双环亚氨基糖是多羟基化十氢吡啶并[1,2- a ] a庚因的衍生物。从二组分偶联反应开始，通过形成硝酮和1，3偶极环加成反应，获得了氮杂双环中间体。在随后的反应序列中，氮杂双环中间体被转化为相应的环氧化物衍生物。N-O键还原性裂解，随后是分子内7-内-tet环化，是导致七元环闭合的关键步骤。另外，探索了使用双环碘化物衍生物的替代合成途径。合成的十氢吡啶并[1,2- a]的抑制活性检查了针对所选糖苷酶的] azepines。