Polymer supported synthesis of a natural product-inspired oxepane library |
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| Institution: | 1. Institute of Virology, Heinrich-Heine-University Düsseldorf, Düsseldorf, Germany;2. Institute for Genetics and Cologne Excellence Cluster on Cellular Stress Responses in Aging-Associated Diseases (CECAD), University of Cologne, Cologne, Germany;3. Institute of Evolutionary Genetics, Heinrich-Heine-University Duesseldorf, Duesseldorf, Germany |
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| Abstract: | Natural product inspired compound collections are prevalidated due to the evolutionary selection of the natural product scaffolds. Their synthesis requires the development of novel strategies amenable to formats suitable for library build-up. We describe a method for the synthesis of an oxepane library inspired by the core structure of oxepane natural products endowed with multiple bioactivities. Core aspects of the strategy are the establishment of a one-pot method employing different immobilized scavengers, the employment of an enyne ring closing reaction and diversification by means of different transformations, for example, cycloadditions and cross-metathesis reactions. In total, a collection of 115 oxepanes was obtained in 5–6-step reaction sequences. |
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| Keywords: | Polymer supported synthesis Oxepane One-pot synthesis Immobilized scavengers Enyne ring closing reaction Cycloaddition Cross-metathesis reaction |
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