[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
AbstractReflection 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.
|Corporate author||Warsaw University of Technology (PW)|
|Journal series||Organic & Biomolecular Chemistry, ISSN 1477-0520|
|Publication size in sheets||0.6|
|ASJC Classification||; ;|
|Score|| = 35.0, 17-08-2020, ArticleFromJournal|
= 35.0, 17-08-2020, ArticleFromJournal
|Publication indicators||= 9; = 8; : 2016 = 0.805; : 2016 = 3.564 (2) - 2016=3.235 (5)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.