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.
View Book: - http://bp.bookpi.org/index.php/bpi/catalog/book/162
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.
View Book: - http://bp.bookpi.org/index.php/bpi/catalog/book/162
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