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A novel and stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate: conduritol-A derivative

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Abstract

The stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate, methyl-substituted dihaloconduritol-A is reported. Bromination of 2-methylbenzo-1,4-quinone followed by the reduction in the carbonyl groups with NaBH4 to give a dioldibromo compound. The diol was converted to diacetates by acetylation with Ac2O-pyridine. Reaction of methyl-dioldibromodiacetate with LiOH gave stereoselectively the monoepoxide compound. Controlled reaction of the epoxide with AcCl in methylene chloride furnished the desired new dihaloconduritol-A derivative which was characterized by spectroscopic methods. All the synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, COSY (2D-NMR), and HRMS analyses.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Arts, Ordu University, 52200, Ordu, Turkey

    Latif Kelebekli & Dilek Kaplan

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  1. Latif Kelebekli
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  2. Dilek Kaplan
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Correspondence to Latif Kelebekli.

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Kelebekli, L., Kaplan, D. A novel and stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate: conduritol-A derivative. J IRAN CHEM SOC 17, 803–808 (2020). https://doi.org/10.1007/s13738-019-01810-3

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  • DOI: https://doi.org/10.1007/s13738-019-01810-3

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