Enzymatic synthesis of a chiral chalcogran intermediate

✍ Scribed by Mastihuba, Vladimír; Čepec, Pavel; Vlčková, Silvia; Farkašová, Erika; Mastihubová, Mária; Bobal, Pavel

• Book ID: 121548823
• Publisher: Versita
• Year: 2014
• Tongue: English
• Weight: 281 KB
• Volume: 68
• Category: Article
• ISSN: 0366-6352
• DOI: 10.2478/s11696-013-0523-5

✦ Synopsis

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.