Lipase Mediated Synthesis of (3R)-Stiripentol | Chapter 6 | Current Research and Development in Chemistry Vol.1

Racemic stiripentone was synthesised from piperonal and pinacolone and reduced to the alcohol stiripentol, which was obtained in high yield. Kinetic resolution of stiripentol catalysed by lipase A from Candida antarctica via esterification with vinyl butanoate has been performed with an E-value of 24. This allowed isolation of (3S)-stiripentol with an enantiomeric excess (ee) of 86% and the corresponding (3R)-butanoate with an ee of 87%. Enzymatic hydrolysis of the ester product gave (3R)-stiripentol with an ee of 94%. Additionally, a novel one-pot two-step pathway for the synthesis of 5-vinylbenzo[d][1,3]dioxole starting from (E)-3,4-dihydroxycinnamic acid has been developed. Lipase catalysed esterification of 4,4-dimethylpent-1-en-3-ol afforded (R)-(+)-4,4-dimethylpent-1-en-3-ol and an ee >99% of (3R)-stiripentol was obtained via cross metathesis of this compound coupled with 5vinylbenzo[d][1,3]dioxole.  

Author(s) Details

Mohammed Farrag El-Behairy
Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Sadat City, Menoufiya, 32897, Egypt

Elisabeth Egholm Jacobsen
Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway.

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