Naturally occurring scaffolds for compound library design: convenient access to bis-aryl 1-azaadamantanes carrying a vicinal amino alcohol motif |
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Authors: | Abuzar Taheri Ronald J Quinn Mikhail Krasavin |
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Institution: | 1. Eskitis Institute for Drug Discovery, Griffith University, Brisbane, Queensland 4111, Australia;2. Department of Chemistry, St. Petersburg State University, 26 Universitetskyi Prospekt, Peterhof 198504, Russian Federation |
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Abstract: | The vast majority of scaffolds found in natural products are absent from the currently available compound collections for biological screening. At the same time, scaffolds derived from natural products may have a distinct advantage over non-natural cores in terms of providing compounds endowed with biological activities and should be used extensively in screening library design. We have developed a synthetic approach to merging a naturally occurring 1-azaadamantane core with a vicinal amino alcohol moiety that is also common in natural product chemical space. The synthesis features diastereoselective epoxidation of racemic chiral 2,6-diaryl-4-methylene 1-azaadamantanes with subsequent SN2-type epoxide opening in aqueous isopropanol. |
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Keywords: | Molecular scaffolds 1-Azaadamantanes Vicinal amino alcohols Aza-Prins reaction Olefin epoxidation Epoxide opening |
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