論文 - 菅本 和寛
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Enantioselective syntheses of 10-oxo-11 (E)-octadecen-13-olide and related fatty acid
Matsushita Y., Sugamoto K., Nakama T., Matsui T., Hayashi Y., Uenakai K.
Tetrahedron Letters 38 ( 34 ) 6055 - 6058 1997年8月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Tetrahedron Letters
The first, and short-step, syntheses of S and R enantiomers of 10-oxo-11(E)octadecen-13-olide (1) and its seco-acid 2, cytotoxic fatty acid derivatives from corn, were achieved from linoleic acid (3) by the combined use of lipoxygenase-catalyzed asymmetric oxygenation and cobalt porphyrin-catalyzed reduction-oxygenation as key-step reactions.
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Facile and general method for preparation of (E)-4-Hydroxy-2-alkenals
Sugamoto K., Matsushita Y., Matsui T.
Lipids 32 ( 8 ) 903 - 905 1997年8月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Lipids
A facile one-pot synthesis of (E)-4-hydroxy-2-alkenals such as (E)-4- hydroxy-2-nonenal, (E)-4-hydroxy-2-heptenal, and (E)-4-hydroxy-2-hexenal was achieved from the corresponding (2E,4E)-2,4-alkadienals by reduction- oxygenation with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst followed by treatment with trimethylphosphite.
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Lipid Peroxidation-derived Hepatotoxic Aldehyde, 4-Hydroxy-2-hexenal, in Fish
Sakai T., Matsushita Y., Sugamoto K., Uchida K.
Bioscience, Biotechnology and Biochemistry 61 ( 8 ) 1399 - 1400 1997年1月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Bioscience, Biotechnology and Biochemistry
Various samples of fish meat were examined for the formation of the hepatotoxic aldehyde, 4-hydroxy-trans-2-hexenal (HHE). HHE was detected in all samples analyzed at the concentration of 1.5–39.3 nmol/g. Yellowtail meat contained more HHE than 4-hydroxy-trans-2-nonenal (HNE). The HHE and malonaldehyde concentration increased during 13 days of storage at 0°C in the meat of yellowtail. On the other hand, no HNE was detected during storage. © 1997, Taylor & Francis Group, LLC. All rights reserved.
DOI： 10.1271/bbb.61.1399
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松井 隆尚, 松下 洋一, 菅本 和寛 [他]
宮崎大學工學部紀要 25 93 - 97 1996年9月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：宮崎大学
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Matsushita Y., Sugamoto K., Nakama T., Matsui T.
Journal of the Chemical Society, Chemical Communications ( 5 ) 567 - 568 1995年12月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Journal of the Chemical Society, Chemical Communications
γ-Hydroperoxy-α,β-unsaturated carbonyl compounds are prepared in good yields by the regioselective hydroperoxygenation of α,β,γ,δ-unsaturated carbonyl compounds with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst.
DOI： 10.1039/C39950000567
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P-63 リノール酸を出発物質とする殺細胞性脂肪酸誘導体の合成(ポスター発表の部)
松下 洋一, 名嘉真 剛, 菅本 和寛, 松井 隆尚, 林 芳樹, 上中居 和男
天然有機化合物討論会講演要旨集 ( 37 ) 642 - 647 1995年9月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：天然有機化合物討論会
We recently isolated (11E)-13-hydroxy-10-oxooctadec-11-enoic acid (1) and its fourteen-membered lactone 2 as cytotoxic constitutents of the extract of corn, but we could not determined their absolute configuration of the asymmetric carbon at C-13. Therefore, for purposes of elucidation of the absolute configuration of natural 1 and 2 and comparison between their cytotoxic behavior, we attempted syntheses of both their R- and S-enantiomers from linoleic acid via lipoxygenase- and cobalt porphyrin-catalyzed oxygenation as key step-reactions. Linoleic acid (3) was converted into (13S, 9Z, 11E)-13-hydroperoxyoctadeca-9,11-dienoic acid (4) by soybean lipoxygenase-catalyzed oxygenation, which was treated with NaBH_4 and then diazomethane to give 13S-hydroxy ester 5. Dienoic esters 6a-c were obtained from 5 by protection of the hydroxy group and allowed to react with oxygen and triethylsilane in the presence of a catalytic amount of cobalt porphyrin followed by acetylation of intermediary hydroperoxides, to afford 10-oxo compounds 7a-c and 12-oxo ones 8a-c: The yield of 7 increased with bulkiness of the protection group of 6. Hydrolysis of 7c by use of lipase and then deprotection gave 13S-keto acid S-1. On the other hand, 13R-keto acid R-1 was synthesized by lipase-catalyzed hydrolysis of the corresponding lactone R-2. (13S, 9Z, 11E)-13-hydroxyoctadeca-9,11-dienoic acid (10), obtained from 3 by lipoxygenase-catalyzed oxygenation and reduction with NaBH_4, was cyclized by the Yamaguchi method and by the Mitsunobu method, to give 14-membered lactones S-11 and R-11, respectively. The cobalt porphyrin-catalyzed oxygenation of S-11 and R-11 produced the corresponding 10-oxo lactones S-2 and R-2. Thus, we synthesized successfully the both enantiomers of 1 and 2 from linoleic acid in short steps and now evaluate their cytotoxic activity in progress.
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Matsushita Y., Sugamoto K., Nakama T., Sakamoto T., Matsui T., Nakayama M.
Tetrahedron Letters 36 ( 11 ) 1879 - 1882 1995年3月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Tetrahedron Letters
α,β,γ,δ-Unsaturated carbonyl compounds were converted regioselectively into γ-hydroxy-α,β-unsaturated carbonyl compounds by reduction-oxygenation with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst followed by treatment with trimethyl phosphite. (±)-6-Hydroxyshogaol and related furanoids isolated from ginger were synthesized via this method. © 1995.
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g-Selective hydroxylation of a,b,g,d-unsaturated carbonyl compounds and its application to syntheses of (±)-6-hydroxyshogaol and related furanoids 査読あり
Yoh-ichi Matsushita, Kazuhiro Sugamoto, Tsuyoshi Nakama, Toshifumi Sakamoto, Takanao Matsui
Tetrahedron Letters 36 1879 - 1882 1995年3月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Synthesis of g-hydroperoxy-a,b-unsaturated carbonyl compounds from a,b,g,d-unsaturated carbonyl compounds by cobalt(II) porphyrin-catalyzed Hydroperoxygenation 査読あり
Yoh-ichi Matsushita, Kazuhiro Sugamoto, T. Nakama, and Takanao Matsui
J. Chem. Soc., Chem. Commun 567 - 568 1995年3月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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MATSUSITA Yoh-ichi, SUGAMOTO Kazuhiro, MATSUI Takanao
Chemistry letters 1993 ( 6 ) 925 - 928 1993年6月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：公益社団法人 日本化学会
Various aromatic olefins and acrylic acid derivatives were converted to benzyl alcohols and α-hydroxyalkanoic acid derivatives in good yields by the reductive oxygenation with oxygen and triethylsilane in the presence of a catalytic amount of cobalt(II) porphyrin followed by treating the reaction mixture with trimethyl phosphite.
DOI： 10.1246/cl.1993.925
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One-pot preparation of alcohols from aromatic olefins and acrylic acid derivatives by cobalt(II) porphyrin-catalyzed reductive oxygenation followed by reduction with trimethyl phosphate 査読あり
Yoh-ichi Matsushita, Kazuhiro Sugamoto, Takanao Matsui
Chemistry Letters 925 - 928 1993年6月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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MATSUSHITA Yoh-ichi, SUGAMOTO Kazuhiro, MATSUI Takanao
Chemistry letters 1992 ( 11 ) 2165 - 2168 1992年11月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：公益社団法人 日本化学会
2,4-Alkadienoic acid derivatives such as ester, amide, and nitrile were converted to the corresponding 4-oxo-2-alkenoic acid derivatives in good yields by the oxygenation with oxygen and triethylsilane in the presence of a catalytic amount of [5,10,15,20-tetra(2,6-dichlorophenyl)porphinato]cobalt(II) followed by acetylation.
DOI： 10.1246/cl.1992.2165
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Novel method for preparation of 4-oxo-2-alkenoic acid derivatives from 2,4-alkadienoic acid derivatives by cobalt(II) porphyrin-catalyzed oxygenation 査読あり
Yoh-ichi Matsushita, Kazuhiro Sugamoto, Takanao Matsui
Chemistry Letters 2165 - 2168 1992年11月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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MATSUSHITA Yoh-ichi, MATSUI Takanao, SUGAMOTO Kazuhiro
Chemistry letters 1992 ( 7 ) 1381 - 1384 1992年7月
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：公益社団法人 日本化学会
An efficient conversion of olefins to ketones was achieved by the use of molecular oxygen and triethylsilane in the presence of a catalytic amount of cobalt(II) complex of porphyrin. The oxidation was accelerated remarkably in alcohols and had chemoselectivity for conjugated olefins.
DOI： 10.1246/cl.1992.1381
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Cobalt(II) porphyrin-catalyzed oxidation of olefins to ketones with molecular oxygen and triethylsilane in 2-propanol 査読あり
Yoh-ichi Matsushita, Kazuhiro Sugamoto, Takanao Matsui
Chemistry Letters 1381 - 1384 1992年6月
記述言語：英語 掲載種別：研究論文（学術雑誌）