The Synthesis of Coenzyme Q
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概要
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A new, efficient synthesis of coenzyme Q is described. The bromination of 2,3-dimethoxy-5-methyl-<I>p</I>-benzoquinone gives 6-bromo-2,3-dimethoxy-5-methyl-<I>p</I>-benzoquinone, which is then converted to the corresponding hydroquinone diacetate by the action of zinc dust in acetic anhydride. 6-Bromo-2,3-dimethoxy-5-methylhydroquinone diacetate is reacted with 1,1-dimethyl-π-allylnickel bromide in hexamethylphosphoramide at 60 °C to afford a 70% yield of 2,3-dimethoxy-5-methyl-6-prenylhydroquinone diacetate, which is hydrogenolyzed with lithium aluminum hydride in ether and then oxidized with aqueous ferric chloride to give coenzyme Q<SUB>1</SUB> in 76% yield. Similarly, coenzyme Q<SUB>2</SUB>, Q<SUB>9</SUB>, and Q<SUB>10</SUB>, and 6′, 10′, 14′-hexahydrocoenzyme Q<SUB>4</SUB> are synthesized by the reaction of the aryl bromide with π-geranyl-, π-solanesyl-, π-decaprenyl-, and π-phytylnickel bromide respectively and by subsequent treatment with LiAlH<SUB>4</SUB> and FeCl<SUB>3</SUB>. The stereochemistry of the products is also described.
- 公益社団法人 日本化学会の論文
著者
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Yamaguchi Ryohei
Department Of Natural Environment Sciences Faculty Of Integrated Human Studies Kyoto University
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Sato Kikumasa
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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Inoue Seiichi
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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SAITO Kenji
Department of Applied Biological Chemistry Graduate School of Agricultural and Life Sciences, The University of Tokyo
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Inoue Seiichi
Department of Applied Chemistry, Faculty of Engineering, Yokohama National University
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Yamaguchi Ryohei
Department of Applied Chemistry, Faculty of Engineering, Yokohama National University
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