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Synlett 1996; 1996(10): 978-980
DOI: 10.1055/s-1996-5638
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Chemo-enzymatic Synthesis of (2R,5S)- and (2R,5R)-5-(1-Hydroxy-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran (‘Linalool Oxide’): Preparative Application of a Highly Selective Bacterial Epoxide Hydrolase

Martin Mischitz* , Kurt Faber
  • *Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria, Fax: +43-316-873-8740, e-mail: <Faber@Orgc.TU-Graz.ac.at>
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Publication Date:
31 December 2000 (online)

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Trans-(2R,5R)- and cis-(2R,5S)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran 4 (‘linalool oxide’) were prepared from (3RS,6R)-2,3-epoxylinalyl acetate 1 via a chemo-enzymatic route. The key step consists in a kinetic resolution of 1 employing an epoxide hydrolase preparation derived from Rhodococcus sp. NCIMB 11216, yielding diol (3R,6R)-2 and epoxide (3R,6R)-1 in excellent d.e. (≥98%). Chemical transformation of the latter gave both isomers of 4 on a preparative scale. The enzyme-catalyzed reaction was shown to proceed in an enantio-convergent fashion by means of O18-labelling studies.

Biotransformation - Epoxide Hydrolase - Rhodococcus NCIMB 11216

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