[1,4]-sigmatropic rearrangement of chiral nitrones and their utilization in the synthesis of new iminosugars.
Org Biomol Chem
; 14(2): 470-482, 2016 Jan 14.
Article
em En
| MEDLINE
| ID: mdl-26563609
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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Inibidores Enzimáticos
/
Imino Açúcares
/
Glucosidases
/
Óxidos de Nitrogênio
Limite:
Humans
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article