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Synlett 1992; 1992(3): 245-246
DOI: 10.1055/s-1992-21330
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Applications of Enzymatically Prepared Homochiral Cyclohexane Building Blocks: Enantioselective Synthesis of Derivatives of Unnatural Shikimic Acid and of Pseudo-α-D-mannopyranose

L. Dumortier* , J. Van der Eycken, M. Vandewalle
  • *University of Gent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S,4), B-9000 Gent, Belgium
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Publikationsdatum:
08. März 2002 (online)

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The utility of (1R,2S,3R,4S)-4-butanoyloxy-2,3-O-isopropylidenecyclohexane-1,2,3-triol [(+)-1] as a homochiral building block is illustrated by its transformation into the unnatural enantiomer of methyl shikimate [(+)-10] and into pseudo-α-D-mannopyranose [(+)-14].