Synthesis and functionalization of bicyclic N,O-acetal scaffolds from furfural.
Bioorg Med Chem
; 23(11): 2721-9, 2015 Jun 01.
Article
em En
| MEDLINE
| ID: mdl-25596167
We have synthesized biologically relevant 6-aza-8-oxa[3.2.1]bicyclooctane scaffolds in a five-step procedure starting from furfural. Besides showing that these scaffolds are amenable to decoration via standard functional group interconversions, we also describe investigations for further functionalization via Lewis acid-mediated N,O-acetal opening, followed by nucleophilic trapping of the resulting intermediate cation. By using different nucleophiles, we have successfully prepared a modest library of 2,6-trans-disubstituted pyrans in good yields and in a highly diastereoselective manner.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Aza
/
Compostos Azo
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Compostos Bicíclicos com Pontes
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Descoberta de Drogas
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Furaldeído
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Acetais
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article