Serviços Personalizados
Journal
Artigo
Indicadores
- Citado por SciELO
- Acessos
Links relacionados
- Similares em SciELO
Compartilhar
Journal of the Mexican Chemical Society
versão impressa ISSN 1870-249X
Resumo
MATEUS, Cristiano R. e COELHO, Fernando. An Alternative Approach to Aminodiols from Baylis-Hillman Adducts: Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol. J. Mex. Chem. Soc [online]. 2005, vol.49, n.2, pp.148-158. ISSN 1870-249X.
We describe herein a new approach for the stereoselective synthesis of broad spectrum antibiotics from Baylis-Hillman adducts. The strategy is based on the preparation of an ene-carbamate directly from a Baylis-Hillman adduct using a Curtius rearrangement reaction. Stereoselective hydroboration furnished a mixture of diastereoisomeric aminoalcohols (syn and anti). After chromatographic separation, the syn diastereoisomer was directly transformed into the antibiotics.
Palavras-chave : chloramphenicol; Baylis-Hillman; fluoramphenicol; thiamphenicol; α-hydroxy-methylketones.