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Synlett 2001; 2001(12): 1905-1908
DOI: 10.1055/s-2001-18742
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New Approaches in the Synthesis of Ulosonic Acids and Analogues

Claudia H. Sugisaki* , Yvan Ruland, Ingrid Le Clezio, Michel Baltas
  • *Synthèse et Physicochimie de Molécules d’Intérêt Biologique, UMR 5068 CNRS - Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse cedex 04, France; Fax: + 33(561)556011; E-mail: baltas@chimie.ups-tlse.fr
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Publication Date:
04 December 2001 (online)

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A direct synthesis of bicyclic precursors of ulosonic acids is achieved by reaction of cis-α,β-epoxyaldehydes with ethyl 2-(trimethylsilyloxy)-2-propenoate in the presence of boron trifluoride diethyl etherate.

aldol reaction - epoxides - higher carbohydrates - ring opening - bicyclic products