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Synthesis of pyrone-annulated 2-oxabicyclo[3.3.1]nonanes by palladium-catalyzed cyclization of 4-hydroxy-2-pyrones with allylic bisacetates |
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| Authors: | Masahiro Yoshida Miki Shibata Saaya Mukae Kouki Kinoshita Kenji Matsumoto Tsukasa Hirokane |
| Institution: | 1. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Nishihama, Yamashiro-cho, Tokushima 770-8514, Japan;2. Graduate School of Pharmaceutical Sciences, Tokushima University, 1-78-1 Sho-machi, Tokushima 770-8505, Japan |
| Abstract: | Cyclization of 4-hydroxy-2-pyrones with allylic bisacetates by a palladium catalyst is described. Pyrone-annulated 2-oxabicyclo3.3.1]nonane derivatives were regioselectively produced from the reaction of 4-hydroxy-2-pyrones with 1,4-diacetoxy-2-cyclohexene at high temperature. The reaction would proceed via a migration of the π-allylpalladium intermediate. |
| Keywords: | Corresponding author Palladium Cyclization π-Allylpalladium Pyrones |
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