A new synthetic access to bicyclic iminosugars-derivatives of polyhydroxy decahydropyrido[1,2-a]azepine
Ewa Mironiuk-Puchalska , Mariola Koszytkowska-Stawińska , Monika Wielechowska , Wojciech Sas
AbstractAn 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.
|Journal series||Tetrahedron Letters, ISSN 0040-4039|
|Publication size in sheets||0.5|
|Keywords in English||Bicyclic azepanes; Decahydropyrido[1,2-a]azepine-derived iminosugars; 7-endo-tetcyclization|
|ASJC Classification||; ;|
|Score|| = 25.0, 17-08-2020, ArticleFromJournal|
= 25.0, 17-08-2020, ArticleFromJournal
|Publication indicators||= 6; = 6; : 2016 = 0.635; : 2016 = 2.193 (2) - 2016=2.026 (5)|
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