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

Luuk Steemers, Martin J. Wanner, Martin Lutz, Henk Hiemstra and Jan H. van Maarseveen ()
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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

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: 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.

Date: 2017
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DOI: 10.1038/ncomms15392

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