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

Abstract

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 ZChO
Ewa Mironiuk-Puchalska,,
- Department Of Organic Chemistry
, Mariola Koszytkowska-Stawińska ZChO
Mariola Koszytkowska-Stawińska,,
- Department Of Organic Chemistry
, Monika Wielechowska ZTiBSL
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Wojciech Sas ZChO
Wojciech Sas,,
- Department Of Organic Chemistry
Journal seriesTetrahedron Letters, ISSN 0040-4039
Issue year2016
Vol57
No2
Pages199-202
Publication size in sheets0.5
Keywords in EnglishBicyclic azepanes; Decahydropyrido[1,2-a]azepine-derived iminosugars; 7-endo-tetcyclization
DOIDOI:10.1016/j.tetlet.2015.11.101
URL http://www.sciencedirect.com/science/article/pii/S0040403915304093
Languageen angielski
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Score (nominal)25
ScoreMinisterial score [Punktacja MNiSW] = 25.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) [Punktacja MNiSW (2013-2016)] = 25.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor [Impact Factor WoS]: 2016 = 2.193 (2) - 2016=2.026 (5)
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