A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction |
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Authors: | Masahiro Mineno Yasuhiro SawaiKazuaki Kanno Naotaka SawadaHideya Mizufune |
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Affiliation: | Chemical Development Laboratories, CMC Center, Takeda Pharmaceutical Company Limited, 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan |
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Abstract: | A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to δ-hydroxy-β-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and β-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. |
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Keywords: | 5,6-Dihydro-4-hydroxy-2-pyrones Double Reformatsky reaction Lactonization Kavalactones |
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