Novel Syntheses of Murrayaquinone A and Furostifoline through 4-Oxygenated Carbazoles by Allene-Mediated Electrocyclic Reactions Starting from 2-Chloroindole-3-carbaldehyde
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概要
- 論文の詳細を見る
The formal total synthesis of murrayaquinone A (1) and the total synthesis of furostifoline (5) were completed by the construction of 4-oxygenated 3-methylcarbazoles 7 based on a new type of electrocyclic reaction through 2-alkenyl-3-allenylindole intermediates 8 derived from the 2-alkenyl-3-propargylindoles 9, starting from 2-chloroindole-3-carbaldehyde (11). The N, O-bisbenzyloxymethyl group of 16c and 22 underwent a Brich reduction followed by treatment with Triton B to produce the known 4-hydroxy-3-methylcarbazole (7a) and 4-hydroxy-3-methylfuro[3, 2-a]carbazole (7b) as precursors of murrayaquinone A (1) and furostifoline (5), respectively. The trifluoromethanesulfonyloxy-3-methylfuro[3, 2-a]carbazole (24), prepared from 7b, was subjected to reductive cleavage to provide furostifoline (5).
- 公益社団法人日本薬学会の論文
- 2001-07-01
著者
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藤本 治宏
千葉大院薬
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Hayashi H
Drug Research Division Dainippon Sumitomo Pharma Co. Ltd.
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Hayashi Hideya
Pharmaceuticals And Biotechnology Laboratory Japan Energy Corporation
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Hayashi H
Pharmaceuticals & Biotechnology Laboratory Japan Energy Corporation
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藤本 治宏
Chiba Univ. Chiba Jpn
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Hibino Satoshi
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
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Choshi Tominari
Fac. Of Pharmacy And Pharmaceutical Sciences Fukuyama Univ.
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Choshi Tominari
Fukuyama University Faculty Of Pharmacy And Pharmaceutical Sciences
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CHOSHI Tominari
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Scie
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NOBUHIRO Junko
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Scie
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HIBINO Satoshi
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Scie
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Hibino Satoshi
Fac. Of Pharmacy And Pharmaceutical Sciences Fukuyama Univ.
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Nobuhiro Junko
Graduate School Of Pharmacy And Pharmaceutical Sciences Faculty Of Pharmacy And Pharmaceutical Scien
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Hagiwara H
Tsukuba Research Laboratories Eisai Co. Ltd.
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HAGIWARA Hitomi
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Scie
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FUJIMOTO Hiroyuki
Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Scie
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