Development of a Practical Multikilogram Production of (<i>R</i>)-Seudenol by Enzymatic Resolution

Abstract

Different enzymatic routes for the production of (R)-seudenol were investigated. The Novozym 435-catalyzed reaction of racemic seudenol with vinyl butyrate proved to be the most promising route. By using vinyl laurate as an acyl donor, (R)-seudenol laurate could be separated from (S)-seudenol by an extractive work-up procedure. A nonaqueous hydrolysis allowed the isolation of pure (R)-seudenol. Scaling up to 7 kg resulted in a robust reproducible process.