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Enzymatic synthesis of a chiral chalcogran intermediate

Vladimír Mastihuba, Pavel Čepec, Silvia Vlčková, Erika Farkašová, Mária Mastihubová, and Pavel Bobal

Institute of Chemistry, Centre for Glycomics, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovakia

 

E-mail: chemvrma@savba.sk

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.

Keywords: chalcogran – S-(+)-1-(2-furyl)-3-pentanol – kinetic resolution – lipase

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0523-5

 

Chemical Papers 68 (6) 745–750 (2014)

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