Enzymatic and Organocatalyzed Asymmetric Aldolization Reactions for the Synthesis of Thiosugar Scaffolds

Authors

  • Johan Fanton,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • Flora Camps,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • José A. Castillo,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • Christine Guérard-Hélaine,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • Marielle Lemaire,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • Franck Charmantray,

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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  • Laurence Hecquet

    1. Clermont Université, Université Blaise Pascal, SEESIB, BP 10448, 63000 Clermont-Ferrand, France, Fax: +33-473407717
    2. CNRS, UMR6504, SEESIB, 63177 Aubière cedex, France
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Abstract

We studied the synthesis of original thiosugar scaffolds by enantioselective aldolization. L-Proline-catalyzed C–C bond formation was the key step in the synthesis of L-erythro-thioketoses (3S,4R), whereas fructose-6-phosphate aldolase-catalyzed reactions yielded the D-threo-thioketose series (3S,4S). By the organocatalytic approach, 5-thio-L-ribulofuranose (1) and 5-deoxy-6-thio-L-psicopyranose (2) were obtained in satisfactory overall yields from 2-haloacetaldehydes, whereas 5-thio-D-xylulofuranose (3) was synthesized in 50 % overall yield by an enzymatic aldolization reaction in only two steps from the same starting material.

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