Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/25206
Type: Artigo de periódico
Title: An alternative approach to aminodiols from Baylis-Hillman adducts: stereoselective synthesis of chloramphenicol, fluoramphenicol and thiamphenicol
Author: Mateus, Cristiano R.
Coelho, Fernando
Abstract: 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.
Descrevemos aqui uma nova interpretação para a espectros de banda larga da síntese estereosseletiva de antibióticos de adutos Baylis-Hillman. A estrategia é baseada na preparação de um eno-carbamato diretamente do aduto Baylis-Hillman, usando um rearranjo de Curtius. A hidroboração estereosseletiva fornece uma mistura de aminoalcools diasteroisomeros (syn e anti). Após separação cromatográfica, o diasteroisomero syn foi diretamente transformado no antibiótico.
Subject: chloramphenicol
Baylis-Hillman
fluoramphenicol
thiamphenicol
alpha-hydroxy-methylketones
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0103-50532005000300012
Address: http://dx.doi.org/10.1590/S0103-50532005000300012
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000300012
Date Issue: 1-Jun-2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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