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Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

  • Gábor Zoltán Elek
    Gábor Zoltán Elek
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
  • Kaur Koppel
    Kaur Koppel
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
    More by Kaur Koppel
  • Dzmitry M. Zubrytski
    Dzmitry M. Zubrytski
    Belarusian State University, Department of Organic Chemistry, Leningradskaya 14, 220050 Minsk, Belarus
  • Nele Konrad
    Nele Konrad
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
    More by Nele Konrad
  • Ivar Järving
    Ivar Järving
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
  • Margus Lopp
    Margus Lopp
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
    More by Margus Lopp
  • , and 
  • Dzmitry G. Kananovich*
    Dzmitry G. Kananovich
    Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia
    *E-mail: [email protected]
Cite this: Org. Lett. 2019, 21, 20, 8473–8478
Publication Date (Web):October 9, 2019
https://doi.org/10.1021/acs.orglett.9b03305
Copyright © 2019 American Chemical Society

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    Abstract

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    A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripotent cyclopropanol precursor. The efficacy of the proposed diversity-oriented approach has been validated by short stereoselective synthesis of natural product chlamydocin, containing a challenging-to-install fragment of (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid (Aoe) and a range of its analogues, derivatives of 2-amino-8-oxodecanoic and 2-aminosuberic acids.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b03305.

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