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Alcohol Dehydrogenase‐Catalyzed Synthesis of Enantiomerically Pure

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Abstract

Starting from ethyl 4‐bromobutyrate, the chemoenzymatic synthesis of 6‐vinyl‐tetrahydro‐pyran‐2‐one has been accomplished. A screening of a number of available alcohol dehydrogenases and intense optimization of reaction parameters enabled us to establish an efficient synthesis of either enantiomer of the vinyllactone with excellent enantiomeric excess (>99%). The scope of possible applications of enantiopure vinyllactones has been verified by subjection to cross‐metathesis resulting in the total synthesis of the insect pheromone (S)‐5‐hexadecanolide and the cytotoxic styryllactone goniothalamine as well as derivatives thereof.
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Document Type: Research Article

Affiliations: Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst Geb. 15.8, 52426 Jülich, Germany, Fax: (+49)-2461-616196

Publication date: 17 September 2012

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