[1,4]-sigmatropic rearrangement of chiral nitrones and their utilization in the synthesis of new iminosugars

Maciej Malinowski , Tomasz Rowicki , Patrycja Guzik , Maciej Gryszel , Sebastian Łapczyński , Monika Wielechowska , Karolina Czerwińska , Izabela Madura , Wojciech Sas

Abstract

Reflection on the epimerization of the α-stereocenter of sugar nitrones leads to the conclusion that the process may occur through [1,4]-sigmatropic rearrangement. Participation of an ionic mechanism was excluded by a deuterium labeling experiment, and DFT calculations showed a reasonable energy barrier for the proposed [1,4]-shift. Products of the intramolecular 1,3-dipolar cycloaddition of the studied nitrones were utilized in the diversity-oriented synthesis of polyhydroxy derivatives of piperidine, indolizidine and quinolizidine. Minimal activity against the screened glucosidases and human melanoma cell lines was observed for some of the obtained compounds.
Author Maciej Malinowski (FC / DOC)
Maciej Malinowski,,
- Department Of Organic Chemistry
, Tomasz Rowicki (FC / DOC)
Tomasz Rowicki,,
- Department Of Organic Chemistry
, Patrycja Guzik (FC / DOC)
Patrycja Guzik,,
- Department Of Organic Chemistry
, Maciej Gryszel (FC / DOC)
Maciej Gryszel,,
- Department Of Organic Chemistry
, Sebastian Łapczyński (FC / DOC)
Sebastian Łapczyński,,
- Department Of Organic Chemistry
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Karolina Czerwińska (FC / CICSST)
Karolina Czerwińska,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Izabela Madura (FC / CICSST)
Izabela Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Wojciech Sas (FC / DOC)
Wojciech Sas,,
- Department Of Organic Chemistry
Corporate authorWarsaw University of Technology (PW)
Journal seriesOrganic & Biomolecular Chemistry, ISSN 1477-0520
Issue year2016
Vol14
No2
Pages470-482
Publication size in sheets0.6
ASJC Classification1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry; 1303 Biochemistry
DOIDOI:10.1039/c5ob01432h
URL http://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob01432h#!divAbstract
Languageen angielski
File
c5ob01432h.pdf 1.67 MB
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 17-08-2020, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 17-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 9; WoS Citations = 8; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.805; WoS Impact Factor: 2016 = 3.564 (2) - 2016=3.235 (5)
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