An alternative approach to aminodiols from Baylis-Hillman adducts: stereoselective synthesis of chloramphenicol, fluoramphenicol and thiamphenicol

Journal of the Brazilian Chemical Society

Cristiano R. Mateus¹  Fernando Coelho¹ 

[1] ,Universidade Estadual de Campinas Instituto de Química Campinas SP ,Brazil

关键词: chloramphenicol;    Baylis-Hillman;    fluoramphenicol;    thiamphenicol;    alpha-hydroxy-methylketones;   

DOI  :  10.1590/S0103-50532005000300012

来源: SciELO

【 摘 要 】

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.

【 授权许可】

CC BY   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License