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Enzymatic synthesis of a chiral chalcogran intermediate |
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| Authors: | Vladimír Mastihuba Pavel Čepec Silvia Vlčková Erika Farkašová Mária Mastihubová Pavel Bobal |
| Affiliation: | 1. Institute of Chemistry, Centre for Glycomics, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovakia 2. TAU-CHEM Ltd., Nobelova 34, 836 05, Bratislava, Slovakia 3. Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho 1/3, 612 42, Brno, Czech Republic |
| Abstract: | Two lipases, Novozyme 435 (lipase B from Candida Antarctica) and Lipozyme TL IM (Thermomyces lanuginosus) were used successfully for the kinetic resolution of racemic 1-(2-furyl)-3-pentanol, the key intermediate in synthesis of the bark beetle pheromone, chalcogran. The desired S-(+)-enantiomer was prepared in enantiomeric excesses higher than 98 % and with yields of 26.3 % and 32.5 %, respectively. Methyl tert-butyl ether and vinyl acetate were found to be the best reaction media and the acetyl donor to achieve fast and effective resolution. |
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