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Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy

Author

Listed:
  • Luuk Steemers

    (Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam)

  • Martin J. Wanner

    (Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam)

  • Martin Lutz

    (Crystal and Structural Chemistry Bijvoet Center for Biomolecular Research, Utrecht University)

  • Henk Hiemstra

    (Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam)

  • Jan H. van Maarseveen

    (Van ‘t Hoff Institute for Molecular Sciences, University of Amsterdam)

Abstract

Due to their well-defined three-dimensional geometry, spiro compounds are widely utilized in drug research. From the central tetrahedral carbon atom, besides the regular structure, an inverted spiro connectivity may be envisioned. Here we disclose the synthesis of this molecule class that we have coined quasi[1]catenanes. Next to their fascinating and aesthetic shape, the higher compactness as compared to regular spiro bicycles is noteworthy. To enable synthetic access to compact entangled multimacrocyclic molecules, we have developed a new strategy. The key element is a template, which is covalently connected to the linear precursors, and spatially directs the sterically congested backfolding macrocyclizations that are required to give quasi[1]catenanes. Similarly, quasi[1]rotaxanes are made.

Suggested Citation

  • Luuk Steemers & Martin J. Wanner & Martin Lutz & Henk Hiemstra & Jan H. van Maarseveen, 2017. "Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy," Nature Communications, Nature, vol. 8(1), pages 1-7, August.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms15392
    DOI: 10.1038/ncomms15392
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