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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.49 n.2 México  2005

 

Article

 

An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol

 

Cristiano R. Mateus and Fernando Coelho*

 

Instituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas - SP, Brazil. * e-mail: coelho@iqm.unicamp.br

 

Received: September 21, 2004
Published on the web: March 15, 2005

 

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.

Keywords: chloramphenicol, Baylis-Hillman, fluoramphenicol, thiamphenicol, α-hydroxy-methylketones

 

Resumo

Descrevemos aqui uma nova interpretação para a espectros de banda larga da síntese estereos-seletiva de antibióticos de adutos Baylis-Hillman. А estrategia é baseada na preparação de um eno-carbamato diretamente do aduto Baylis-Hillman, usando um rearranjo de Curtius. А hidroboração estereosseletiva fornece uma mistura de aminoalcools diasteroisomeros (syn e anti). Após separação cromatográfica, o diasteroisomero syn foi diretamente transformado no antibiótico.

 

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Acknowledgments

The authors thank Fapesp for a fellowship to CRM (01/01558-8) and for financial support (02/00461-3) and CNPq (301369/1989-9) for a research fellowship to FC. The authors are grateful to Prof. C. H. Collins for English corrections of this manuscript.

 

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