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Molecules 2016, 21(11), 1552; doi:10.3390/molecules21111552

Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
2
Central Laboratory of the Instrumental Analysis, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 11 October 2016 / Revised: 7 November 2016 / Accepted: 11 November 2016 / Published: 23 November 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [953 KB, uploaded 23 November 2016]   |  

Abstract

Two novel and convenient routes to obtain enantiomerically enriched trans-β-aryl-δ-hydroxy-γ-lactones 5ad with potential antifeedant and anticancer activity were developed. In the first method starting from corresponding enantiomers of γ,δ-unsaturated esters 4ad derived from enzymatically resolved allyl alcohols 1ad, both enantiomers of hydroxylactones 5ad were synthesized with high enantiomeric excesses (73%–97%). Configurations of the stereogenic centers of the synthesized compounds were assigned based on the mechanism of acidic lactonization of esters 4ad in the presence of m-chloroperbenzoic acid (m-CPBA). An alternative method for the production of optically active trans-β-aryl-δ-hydroxy-γ-lactones 5ad was lipase-catalyzed kinetic resolution of their racemic mixtures by transesterification with vinyl propionate as the acyl donor. The most efficient enzyme in the screening procedure was lipase B from Candida antarctica. Its application on a preparative scale after 6 h afforded unreacted (+)-(4S,5R,6S)-hydroxylactones 5ad and (+)-(4R,5S,6R)-propionates 6ad, most of them with high enantiomeric excesses (92%–98%). Resolution of lactone 5d with bulky 1,3-benzodioxol ring provided products with significantly lower optical purity (ee = 89% and 84% for hydroxylactone 5d and propionate 6d, respectively). The elaborated methods give access to both enantiomers of trans-β-aryl-δ-hydroxy-γ-lactones 5ad with the defined absolute configurations of stereogenic centers, which is crucial requirement for the investigations of relationship: spatial structure–biological activity. View Full-Text
Keywords: hydroxylactones; kinetic resolution; lipases hydroxylactones; kinetic resolution; lipases
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Skrobiszewski, A.; Gładkowski, W.; Maciejewska, G.; Wawrzeńczyk, C. Chemoenzymatic Synthesis of trans-β-Aryl-δ-hydroxy-γ-lactones and Enzymatic Kinetic Resolution of Their Racemic Mixtures. Molecules 2016, 21, 1552.

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