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| 1.
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Yamada, Fumio ; Goto, Aya ; Hasegawa, Masakazu ; Kobayashi, Kensuke ; Somei, Masanori ; 山田, 文夫 ; 染井, 正徳
概要:
金沢大学医薬保健研究域薬学系<br />Various nucleophiles, such as indole, 1,2,3-trimethoxybenzene, anisole, phenol, and pyrrole, reacted
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with 1-hydroxy-Nb-trifluoroacetyltryptamine under the presence of mesyl chloride to give novel series of (3a,8acis)- 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles having a substituent at the 3aposition. Their structures and by-products were strictly determined. © 2017 The Japan Institute of Heterocyclic Chemistry.<br />Embargo Period 12 months
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| 2.
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Somei, Masanori ; Iwaki, Takako ; Yamada, Fumio ; Tanaka, Yoshio ; Shigenobu, Koki ; Koike, Katsuo ; Suzuki, Nobuo ; Hattori, Atsuhiko
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />According to the definition of the ideal synthetic method, an example aimed at
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the leads for an α2 blocker, an inhibitor of platelet aggregation, and an anti-osteoporosis agent is established starting from tryptamine. The originality rate, the intellectual property, and the application potential factors of the method are 71, 54, and 100, respectively. The method employs only conventional reagents and reaction conditions without using any protecting groups.{A figure is presented}. © 2006 The Japan Institute of Heterocyclic Chemistry
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| 3.
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Yamada, Fumio ; Fukui, Yoshikazu ; Iwaki, Takako ; Ogasawara, Sachiko ; Okigawa, Masaki ; Tanaka, Satomi ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A simple and new method for the preparation of optically active methyl 3a-chlor
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o-, 3a-bromo-, 3a-hydroxy-, and 3a-alkoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylates has been developed. © 2006 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 4.
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Yamada, Koji ; Tomioka, Saori ; Tanizawa, Noriko ; Somei, Masanori
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金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Hydroxy-6- and -5-nitroindole-3-carbaldehydes are prepared for the first time
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from 1-methoxy-6- and -5-nitroindole-3-carbaldehydes, respectively, based on the discovery of novel methyl ether cleavage reaction. Utilizing them as common synthetic intermediates, syntheses of several daikon-phytoalexin analogs are achieved.
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| 5.
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Fukui, Yoshikazu ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />3-Substituted (3S,6S)-6-(1-hydroxyindol-3-ylmethyl)-2,5-piperazinediones are pr
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epared for the first time. They are shown to be suitable intermediates for the synthesis of 3,10b-disubstituted (3S,5aR,10bS,11as)-1,3,4,5a,6,10b,11, 11a-octahydro-2H-pyrazino[1',2': 1,5]pyrrolo[2,3-b]indole-1,4-dione derivatives.
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| 6.
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Yamada, Fumio ; Goto, Aya ; Peng, Wu ; Hayashi, Toshikatsu ; Saga, Yoshitomo ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A novel nucleophilic substitution reaction at the 1-position of indole nucleus
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was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed.
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| 7.
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Yamada, Koji ; Kanbayashi, Yukiko ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Syntheses of wasabi phytoalexin analogs, such as 6-bromo-5-iodo, 2-bromo-5-iodo
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, 6-nitro, 5-chloroacetyl, and 6-chloroacetyl congeners, are reported. An interesting effect of the 1-methoxy group on the regioselectivity of electrophilic substitution reactions on indole nucleus is observed.
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| 8.
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Somei, Masanori ; Yamada, Fumio ; Goto, Aya ; Hayashi, Masumi ; Hasegawa, Masakazu
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金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 9.
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Yamada, Koji ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />Nucleophiles react with 1-methoxy-3-(2-nitrovinyl)indole (3) at the 2-position regioselectiv
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ely in a dipolar aprotic solvent (DMF or HMPA), while in THF they undergo Michael addition to the β-carbon of nitrovinyl side chain. Depending on bases employed, the resultant Michael addition products (6d, 10, and 11) are found to undergo interesting cyclizations to give novel 3-substituted 1-methoxyindoles (7, 9, and 12).
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| 10.
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Somei, Masanori ; Noguchi, Koichi ; Yamagami, Ryutaro ; Kawada, Yumiko ; Yamada, Koji ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Novel 9-hydroxy-β-carboline derivatives were produced for the first time. A nov
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el rearrangement reaction of 1, 2, 3, 4-tetrahydro-9-hydroxy-β-carbolines was discovered to give 3, 3-disubstituted oxindoles, which was successfully applied to the total synthesis of (±)-coerulescine.
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