Abstract

MATEUS, Cristiano R.  and  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.

Keywords : chloramphenicol; Baylis-Hillman; fluoramphenicol; thiamphenicol; α-hydroxy-methylketones.

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