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. ©2005 Sociedade Brasileira de Química.
CITATION STYLE
Mateus, C. R., & Coelho, F. (2005). An alternative approach to aminodiols from Baylis-Hillman adducts. Stereoselective synthesis of chloramphenicol, fluoramphenicol and thiamphenicol. Journal of the Brazilian Chemical Society, 16(3 A), 386–396. https://doi.org/10.1590/S0103-50532005000300012
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