Horner-Emmons olefination of 4-hydroxy-2-oxoalkylphosphonates and related compounds: Applications to the syntheses of (.+-.)-gingerol, (.+-.)-yashabushiketol, and (.+-.)-dihydroyashabushiketol.
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概要
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Horner–Emmons olefination of 4-hydroxy-2-oxoalkylphosphonates, readily available by hydrogenation of 5-substituted 3-phosphinylmethyl-2-isoxazolines, gives mainly E-isomers of 1-hydroxy-4-alken-3-ones bearing a variety of substituents at the 1-position. Use of the combination of triethylamine (or DBU)+lithium bromide as a weak base on the <I>O</I>-unprotected phosphonates is favored. Similar olefinations on the isoxazolines, 2-oxo-3-alkenylphosphonates, and 4-alkoxy-2-oxoalkylphosphonates have been also examined. Their synthetic applications to (±)-Gingerol, (±)-Yashabushiketol, and (±)-Dihydroyashabushiketol are described.
- 公益社団法人 日本化学会の論文
著者
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SUGA Hiroyuki
Institute for Medical and Dental Engineering, Tokyo Medical and Dental University
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Kanemasa Shuji
Institute Of Advanced Material Study Kyushu University
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Tsuge Otohiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences
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Nakagawa Norihiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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