Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method |
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| Affiliation: | 1. Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey;2. Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey;1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;2. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary;3. Department of Biochemistry, University of Szeged, Dóm tér 9, H-6720 Szeged, Hungary;1. Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan;2. International Institute for Carbon-Neutral Energy Research (I2CNER), Kyushu University, Fukuoka 819-0395, Japan |
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| Abstract: | Racemic α′-acetoxy α,β-unsaturated cyclohexanone has been converted to the corresponding enantiomerically enriched α′-hydroxylated and acetoxylated compounds with 97% ee via enzymatic resolution with PLE. OsO4-Catalyzed dihydroxylation of enantiomerically enriched α′-acetoxylated compound afforded a single diastereomer in 85% chemical yield. The absolute configuration of 2,3,6-triacetoxycylohexanone was determined by X-ray diffraction analysis. Subsequent Luche reduction allowed us to obtain corresponding syn-type cyclitol precursors in a highly stereoselective manner as expected. |
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