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

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 co...

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Autores principales: Steemers, Luuk, Wanner, Martin J., Lutz, Martin, Hiemstra, Henk, van Maarseveen, Jan H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458513/
https://www.ncbi.nlm.nih.gov/pubmed/28541349
http://dx.doi.org/10.1038/ncomms15392
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author Steemers, Luuk
Wanner, Martin J.
Lutz, Martin
Hiemstra, Henk
van Maarseveen, Jan H.
author_facet Steemers, Luuk
Wanner, Martin J.
Lutz, Martin
Hiemstra, Henk
van Maarseveen, Jan H.
author_sort Steemers, Luuk
collection PubMed
description 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.
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spelling pubmed-54585132017-07-11 Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy Steemers, Luuk Wanner, Martin J. Lutz, Martin Hiemstra, Henk van Maarseveen, Jan H. Nat Commun Article 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. Nature Publishing Group 2017-05-25 /pmc/articles/PMC5458513/ /pubmed/28541349 http://dx.doi.org/10.1038/ncomms15392 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Steemers, Luuk
Wanner, Martin J.
Lutz, Martin
Hiemstra, Henk
van Maarseveen, Jan H.
Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title_full Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title_fullStr Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title_full_unstemmed Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title_short Synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
title_sort synthesis of spiro quasi[1]catenanes and quasi[1]rotaxanes via a templated backfolding strategy
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458513/
https://www.ncbi.nlm.nih.gov/pubmed/28541349
http://dx.doi.org/10.1038/ncomms15392
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