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Stereoselective synthesis of 1-methyl-1,2-and 1,3-cyclopentanediols via γ-lactones

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of 1-methylcarbapentofuranose derivatives was developed, where 1,2-cis- and 1,2-trans-4-hydroxymethyl-1-methylcyclopentanediols were obtained from intramolecular opening of a 4-epoxy-4-methyl-γ-lactone. An intramolecular aldol reaction of 4-methyl-4-(2-oxoethyl)-γ-lactone derivatives yielded 1,3-cis- and 1,3-trans-4-hydroxymethyl-1-methylcyclopentanediols.

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Authors and Affiliations

  1. Cambrex Tallinn AS, 3/1 Teaduspargi, Tallinn, 12618, Estonia

    A. Niidu

  2. Tallinn University of Technology, 15 Akadeemia tee, Tallinn, 12618, Estonia

    A. Paju, A.-M. Müürisepp, I. Järving, T. Kailas & M. Lopp

  3. National Institute of Chemical Physics and Biophysics, 23 Akadeemia tee, Tallinn, 12618, Estonia

    T. Pehk

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  1. A. Niidu
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  2. A. Paju
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  3. A.-M. Müürisepp
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  4. I. Järving
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  5. T. Kailas
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  6. T. Pehk
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  7. M. Lopp
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Correspondence to M. Lopp.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1871-1880, December, 2012.

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Niidu, A., Paju, A., Müürisepp, AM. et al. Stereoselective synthesis of 1-methyl-1,2-and 1,3-cyclopentanediols via γ-lactones. Chem Heterocycl Comp 48, 1751–1760 (2013). https://doi.org/10.1007/s10593-013-1206-4

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  • DOI: https://doi.org/10.1007/s10593-013-1206-4

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