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A Short and Efficient Asymmetric Synthesis of (±)-epi-Cytoxazone from cis-(1R,2S,5R)-Menthyl 4-Methoxyphenylglycidates

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Chemistry of Natural Compounds Aims and scope

The racemic epi-cytoxazone was synthesized, starting from p-anisaldehyde, in five steps and 48% overall yield. An efficient synthesis of azido alcohols has been achieved by regioselective ring opening of glycidates using NaN3 in MeOH–H2O. The key step of the process is reductive cyclization of azide carbonates by Zn–TMSCl.

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Acknowledgment

The Uludap University Research Fund is gratefully acknowledged for its financial support (Project No 2001-2).

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Authors and Affiliations

  1. Mus Alparslan University, Department of Chemistry, 49100, Mus, Turkey

    Mustafa Er

  2. Uludag University, Department of Chemistry, 16059, Bursa, Turkey

    Necdet Coskun

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  1. Mustafa Er
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  2. Necdet Coskun
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Correspondence to Mustafa Er.

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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2014, pp. 932–935.

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Er, M., Coskun, N. A Short and Efficient Asymmetric Synthesis of (±)-epi-Cytoxazone from cis-(1R,2S,5R)-Menthyl 4-Methoxyphenylglycidates. Chem Nat Compd 50, 1071–1074 (2014). https://doi.org/10.1007/s10600-014-1161-z

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  • DOI: https://doi.org/10.1007/s10600-014-1161-z

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