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Molecules 2018, 23(5), 1090; https://doi.org/10.3390/molecules23051090

Traceless Solid-Phase Synthesis of [6,7,8 + 5,6,7]-Fused Molecular Frameworks

1
Department of Organic Chemistry, Faculty of Science, Palacky University, 17. Listopadu 12, 771 46 Olomouc, Czech Republic
2
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USA
*
Author to whom correspondence should be addressed.
Received: 14 April 2018 / Revised: 30 April 2018 / Accepted: 2 May 2018 / Published: 4 May 2018
(This article belongs to the Special Issue Solid Phase Synthesis)
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Abstract

We report two synthetic strategies for traceless solid-phase synthesis of molecular scaffolds comprising 6- to 8-membered rings fused with 5- to 7-membered rings. Traceless synthesis facilitated preparation of target molecules without any trace of polymer-supported linkers. The cyclization proceeded via acid-mediated tandem N-acylium ion formation followed by the nucleophilic addition of O- and C-nucleophiles. The presented synthetic strategy enabled, through the use of simple building blocks without any conformational preferences, the evaluation of the predisposition of different combinations of ring sizes to form fused ring molecular scaffolds. Compounds with any combination of [6,7 + 5,6,7] ring sizes were accessible with excellent crude purity. The 8-membered cyclic iminium was successfully fused only with the 5-membered cycle and larger fused ring systems were not formed, probably due to their instability. View Full-Text
Keywords: bicyclic compounds; heterocycles; iminiums; scaffold; solid-phase synthesis bicyclic compounds; heterocycles; iminiums; scaffold; solid-phase synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Giménez-Navarro, V.; Krchňák, V. Traceless Solid-Phase Synthesis of [6,7,8 + 5,6,7]-Fused Molecular Frameworks. Molecules 2018, 23, 1090.

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