Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives |
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Authors: | Solenn Brajeul Christian Marazano |
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Affiliation: | Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France |
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Abstract: | In search for new methods aiming biomimetic synthesis of polyprenylated acylphloroglucinols (PPAPs), we now report the results of an evaluation of sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives, in neutral conditions. As a result, conditions were found for rather efficient C-prenylation of these compounds. The corresponding trimethyl ether gave the best results, but the reaction was accompanied by a deacylation process. Geranyl transfer was also observed, but in low yield, and, interestingly, an isolavandulyl group could be introduced with an appreciable yield. |
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Keywords: | Benzoylphloroglucinol Sulfonium salts Biomimetic synthesis Prenyl transfer Friedel-Crafts alkylation |
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