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


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.
Author Ewa Mironiuk-Puchalska (FC / DOC)
Ewa Mironiuk-Puchalska,,
- Department Of Organic Chemistry
, Mariola Koszytkowska-Stawińska (FC / DOC)
Mariola Koszytkowska-Stawińska,,
- Department Of Organic Chemistry
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Wojciech Sas (FC / DOC)
Wojciech Sas,,
- Department Of Organic Chemistry
Journal seriesTetrahedron Letters, ISSN 0040-4039
Issue year2016
Publication size in sheets0.5
Keywords in EnglishBicyclic azepanes; Decahydropyrido[1,2-a]azepine-derived iminosugars; 7-endo-tetcyclization
ASJC Classification1605 Organic Chemistry; 3002 Drug Discovery; 1303 Biochemistry
URL http://www.sciencedirect.com/science/article/pii/S0040403915304093
Languageen angielski
1-s2.0-S0040403915304093-main.pdf 541.94 KB
Score (nominal)25
Score sourcejournalList
ScoreMinisterial score = 25.0, 17-08-2020, ArticleFromJournal
Ministerial score (2013-2016) = 25.0, 17-08-2020, ArticleFromJournal
Publication indicators WoS Citations = 6; Scopus Citations = 6; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.635; WoS Impact Factor: 2016 = 2.193 (2) - 2016=2.026 (5)
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