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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