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Issue 43, 2012
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Stereoconvergent route to chiral cyclohexenone building blocks: formal synthesis of (−)-dysidiolide

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Abstract

A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1 : 1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (−)-dysidiolide.

Graphical abstract: Stereoconvergent route to chiral cyclohexenone building blocks: formal synthesis of (−)-dysidiolide

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Publication details

The article was received on 03 Aug 2012, accepted on 12 Sep 2012 and first published on 08 Oct 2012


Article type: Paper
DOI: 10.1039/C2OB26532J
Citation: Org. Biomol. Chem., 2012,10, 8609-8615
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    Stereoconvergent route to chiral cyclohexenone building blocks: formal synthesis of (−)-dysidiolide

    G. A. I. Moustafa, Y. Kamada, T. Tanaka and T. Yoshimitsu, Org. Biomol. Chem., 2012, 10, 8609
    DOI: 10.1039/C2OB26532J

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