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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 ; Hasegawa, Toshifumi ; Wakita, Masayuki ; Sugiyama, Mitsuru ; 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
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| 4.
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Somei, Masanori ; Yamada, Fumio ; Ohnishi, Hiroyuki ; Makita, Yoshihiko ; Kuriki, Mikako
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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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| 5.
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Somei, Masanori ; Sayama, Shinsuke ; Naka, Katsumi ; Yamada, Fumio
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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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| 6.
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Somei, Masanori ; Yamada, Fumio ; Kunimoto, Masako ; Kaneko, Chikara
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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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| 7.
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Somei, Masanori ; Yamada, Fumio ; Makita, Yoshihiko
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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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| 8.
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Somei, Masanori ; Yamada, Fumio
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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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Somei, Masanori ; Iwasa, Etsuo ; Yamada, Fumio
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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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| 10.
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Somei, Masanori ; Yamada, Fumio ; Hamada, Hirokazu ; Kawasaki, Toshiya
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
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| 11.
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Yamada, Fumio ; Saida, Yoshihiro ; 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
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| 12.
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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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| 13.
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Yamada, Fumio ; Tamura, Mayumi ; 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 preparative method of psilocin was established in only five steps from indole-3-carbaldehyde in 50% overall yield.
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| 14.
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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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| 15.
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Somei, Masanori ; Hamamoto, Shoichi ; Nakagawa, Kyoko ; Yamada, Fumio ; Ohta, Toshiharu
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
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| 16.
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Somei, Masanori ; Yamada, Yoshikazu ; Kitagawa, Keiichi ; Sugaya, Katsuko ; Tomita, Yayoi ; Yamada, Fumio ; Nakagawa, Kyoko
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 />2-Amino-4-(1-methylindol-3-yl)thiazole (11c) has a characteristic nucleophilic
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nature at the 5-position and add to the 4-position of acetylpyridinium acetate (13) producing 2-acetylamino-5-(1-acetyl-1,4-dihydropyridin-4-yl)-4-(1-methylindol-3-yl) thiazole (1c). Its structure was established by X-ray single crystallographic analysis. Applying the results, simple syntheses of the related tris- (1a-b and 2-8) and tetrakis-linked heterocycles (9) were achieved.
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| 17.
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Somei, Masanori ; Yamada, Fumio ; Goto, Aya ; Hayashi, Masumi ; Hasegawa, Masakazu
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
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| 18.
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Somei, Masanori ; Yamada, Fumio ; Izumi, Tomoyuki ; Nakajou, Masahiro
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 />1-Methoxy-3-(2-nitrovinyl)indole (4) functions as an electrophile and reacted w
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ith various nucleophiles regioselectively at the 2-position. Employing allyl alkoxides as nucleophiles, a novel synthetic method of pyrrolo[2,3-b]indoles has been elaborated. Utilizing the method, the synthesis of (±)-debromofIustramine B (10b) was achieved.
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| 19.
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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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| 20.
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Yamada, Fumio ; Hamabuchi, Shin ; Shimizu, Aya ; 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
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| 21.
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Somei, Masanori ; Kawasaki, Toshiya ; Fukui, Yoshikazu ; Yamada, Fumio ; Kobayashi, Tetsuya ; Aoyama, Harumi ; Shinmyo, Daisuke
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
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| 22.
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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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| 23.
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Somei, Masanori ; Tanimoto, Asuka ; Orita, Hitomi ; Yamada, Fumio ; Ohta, Toshiharu
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 synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalex
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in isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.
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| 24.
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Somei, Masanori ; Yamada, Fumio ; Suzuki, Yoshiaki ; Ohmoto, Shinobu ; Hayashi, Hiroyuki
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 />For evaluating the effectiveness of organic synthesis, both intellectual property factor (IP
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F) and application potential factor (APF) are proposed. As a representative example, a highly effective synthetic method with IPF value of 53.8 and APF value of 100 has been established starting from indigo directing toward an antibiotic, 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole, using only conventional reagents without using any protecting groups. © 2004 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 25.
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Somei, Masanori ; Morikawa, Harunobu ; 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 />1-Hydroxytryptamines (6a-f) having (E)-3-phenyl-, (E)-3-(4-hydroxyphenyl)-, (E)
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-3-(4-hydroxy-3-methoxyphenyl)propenoyl, octanoyl, hexadecanoyl, and docosanoyl group as a Nb-substituent are prepared for the first time. Preparations of serotonins (2a-c, e) from the corresponding 1-hydroxytryptamines (6a-c, e) are also reported. A novel homologation on the 3-substituent of 1-hydroxytryptamines is discovered upon treatment with diazomethane in chloroform or dichloromethane.
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| 26.
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Yamada, Fumio ; Hashizume, Tomoko ; 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 />One step conversion method of indole-3-carboxaldehydes into indole-3-acetonitri
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les is developed. Applying the method, 4-nitro- (7 a), 4-phenyl-(7 b), 4-iodo- (7 c), 4-methoxy- (7 d), and 4-benzyloxyindole-3-acetonitrile (7 e) are available in two steps from indole-3-carboxaldehyde (4).
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| 27.
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Nakai, Yu-ya ; Goto, Aya ; 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 />金沢大学薬学部<br />Syntheses of N-2-(1-hydroxyindol-3-yl)ethyl-1-hydroxyindole-3-acetamide (3a) an
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d -indole-3-acetamide (4a) are reported. They undergo nucleophilic substitution reaction at the 1-position upon reaction with indole in 85% formic acid to give new type compounds, N-2-[1-(indol-3-yl)indol-3-yl]ethylindole-3-acetamide (13), N-2-(indol-3-yl)ethyl-(14), and N-2-[1-(indol-3-yl)indol-3-yl]ethyl-1-(indol-3-yl)indole-3-acetamide (15).
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| 28.
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; 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 />1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile substrate fo
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r the nucleophilic substitution reactions providing 2,3,6-trisubstituted indole derivatives. Preparation of a novel pyrimido[1,2-a]indole derivative is also reported.
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| 29.
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Yamada, Fumio ; Hayashi, Toshikatsu ; Yamada, Koji ; 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 lithium hydroxide promoted glucosidation of 1-hydroxyindoles with 2, 3, 4, 6-
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tetra-0-acetyl-α-D-glucopyranosyl bromide is newly developed. Applying this method, the first and simple syntheses of novel indol-1-yl glucosides were achieved.
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| 30.
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Yamada, Fumio ; Kobayashi, Kensuke ; Shimizu, Aya ; Aoki, Naokatsu ; 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
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| 31.
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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 />1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nit
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rogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.<br />An easy approach to 7-substituted 4,5-dihydro-7H-pyrano[3,4-c]-isoxazole derivatives (3a-b and 6a-d) is described by the reaction of 2-aryl substituted 1-nitro-3-oxa-6-heptynes (2, 5a and 5b) with n-BuLi, followed by treatment with acetic anhydride.
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| 32.
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Somei, Masanori ; Yamada, Fumio ; Morikawa, Harunobu
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
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| 33.
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Hasegawa, Masakazu ; Tabata, Matsuko ; Satoh, Keiichi ; 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 />金沢大学薬学部<br />1-Hydroxyindoles are sensitive to acids and undergo four types of competing rea
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ctions; dehydroxylation, nucleophilic substitution, dimerization, and formation of hexacyclic dimer. The direction of the reaction seems to be determined depending on the subtle balance of substrate structures, acids, and reaction conditions. Stuctures of variety of products are unequivocally determined by X-ray single crystallographic analyses and chemical correlations.
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| 34.
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Somei, Masanori ; Nakajou, Masahiro ; Teramoto, Tsuyoshi ; Tanimoto, Asuka ; 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 />A simple synthetic route was established for 3-acetyl-1-methoxyindole, which wa
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s found to undergo nucleophilic substitution reactions selectively at the 2-position. Applying the reaction, novel 2-substituted methyl 2,3- dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates were prepared.
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| 35.
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Somei, Masanori ; Yamada, Fumio ; Kato, Jun ; Suzuki, Yoshiaki ; Ueda, Yoshinori
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 />Their Diels-Alder reaction produced 11-alkyl-, 11-allyl-, and 11-β-glycosylindo
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lo[2,3-a]carbazoles. Formation of a novel 6,7-dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine derivative is also reported.
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| 36.
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Yamada, Fumio ; Fukui, Yoshikazu ; Shinmyo, Daisuke ; 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
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| 37.
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Somei, Masanori ; Noguchi, Koichi ; 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 />1-Hydroxyyohimbine was prepared for the first time. Its skeletal rearrangement
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reaction either directly into 2-oxindole or into 3-oxindole derivatives by a series of reaction is reported. 1-Hydroxyyohimbine and some of its derivatives showed potent α2 blocking activity.
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| 38.
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Yamada, Koji ; Izumi, Tomoyuki ; 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 />金沢大学薬学部<br />1-Methoxy-3-(2-nitrovinyl)indole (1a) functions as an electrophile and reacts w
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ith various nucleophiles. In THF, nucleophiles undergo conjugate addition to the β-carbon of the nitroviyyl side chain of 1a, regioselectively. The resultant Michael addition products (4d and 8) cyclize to novel 3-substituted 1-methoxyindoles (5 and 7) depending on reaction conditions and a plausible mechanism is discussed. In dipolar aprotic solvent (DMF), nucleophiles react with 1a at the 2-position predominantly with concomitant liberation of the 1-methoxy group giving 2-substituted indoles. © 2005 The Japan Institute of Heterocyclic Chemistry.
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| 39.
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Somei, Masanori ; 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 />A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3- acetoni
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trile with 2,3,4, 6-tetra-O-acetyl-a-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.
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| 40.
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Somei, Masanori ; Oshikiri, Naoki ; Hasegawa, Masakazu ; 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 />A unique synthetic method for melatonin was established through biologically pr
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omising synthetic intermediates. 1-Hydroxymelatonin was prepared as crystals for the first time. It reacted with 85% formic acid to give (±)-3a,3a'-bispyrrolo[2,3-b]indole compound, whose structure was unequivocally determined by X-Ray crystallographic analysis
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| 41.
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Iwaki, Takako ; Fujita, Yasuaki ; 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 />金沢大学薬学部<br />1-(β-D-Xylopyranosyl)- (2a), 1-(β-D-glucopyranosyl)- (2b), 1-(β-D-galactopyrano
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syl)- (2c), and 1-(α-D-arabinopyranosyl)melatonins (3b) are prepared as water-soluble melatonins starting from melatonin.
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| 42.
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Yamada, Fumio ; Goto, Aya ; 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 convenient synthetic methodology for 3a-(indol-3-yl)- 1,2,3,3a,8,8
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a-hexahydropyrrolo[2,3-b]indole, the core structure of leptosins D-F is developed by applying nucleophilic substitution reaction of 1- hydroxytryptamines.
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| 43.
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Somei, Masanori ; Yamada, Fumio ; Hayashi, Toshikatsu ; Goto, Aya ; Saga, Yoshitomo
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 />1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction
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of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanism on the indole nitrogen is proposed.
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| 44.
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Hayashi, Toshikatsu ; Nakai, Yu-ya ; 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 />金沢大学薬学部<br />A novel synthetic method is discovered for 3-hydroxy-3H-indole-3-ethanamines an
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d -3H-indole-3-acetamides having either a 4-morpholinyl or 1-pyrrolidinyl group at the 2-position by reacting the corresponding 1-hydroxyindoles with enamines in the presence of tosyl or mesyl chloride. A plausible mechanism is proposed.
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| 45.
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Iwaki, Takako ; Yamada, Fumio ; Funaki, Shiho ; 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 />Three methods have been newly developed for the synthesis of 1,2,3,3a,8,8a-hexa
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hydropyrrolo[2,3-b]indoles. Employing them, 3a-chloro-, 3a-bromo-, 3a-hydroxy-, and various 3a-alkoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2, 3-b]indoles are now readily available.
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| 46.
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Somei, Masanori ; Noguchi, Koichi ; Yoshino, Katsumasa ; Mori, Koichiro ; Asada, Mamiko ; Yamada, Fumio ; Tanaka, Yoshio ; Shigenobu, Koki ; Koike, Katsuo
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
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| 47.
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Yamada, Fumio ; Yamada, Koji ; Takeda, Hikari ; 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 />Preparations of 5-nitroindol-1-yl (5a), 6-nitroindol-1-yl (5b), and 1,2,3-benzo
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triazol-1-yl 1-methoxyindole-3-carboxylates (9) are reported. These are active esters and proved to be useful intermediates for the preparations of ester and amide analogs of methyl 1-methoxyindole-3-carboxylate, a wasabi phytoalexin.
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| 48.
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Yamada, Fumio ; Shinmyo, Daisuke ; Nakajou, Masahiro ; Somei, Masanori
概要:
1-Methoxyindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position wi
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th various types of nucleophiles providing 2-substituted indole-3-carbaldehydes. © 2012 The Japan Institute of Heterocyclic Chemistry.
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| 49.
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Somei, Masanori ; Kizu, Kiyomi ; Kunimoto, Masako ; Yamada, Fumio
概要:
Various 4-halogeno-3-indoleacetic acids and -3-indoleacetonitriles were synthesized for the first time by means of the Sandmeyer or Schiemann reaction, demonstrating the versatility of 4-indolediazonium salts in 4-substituted indole
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chemistry. A practical synthetic method for 4-halogenoindoles was developed by regio-selective thallation-halogenation, and the products were also led to 4-halogeno-3-indoleacetic acids. The first synthesis of 4-formyl-3-indoleacetonitrile is also reported.
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| 50.
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Somei, Masanori ; Teranishi, Sakiko ; Yamada, Koji ; Yamada, Fumio
概要:
Serotonins were found to produce 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles by simple heating with am
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ines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles rather than β-carbolines under basic conditions. In these novel reactions, the presence of the 5-hydroxy group on the indole nucleus was suggested to be essential. Possible mechanisms are discussed.
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| 51.
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Somei, Masanori ; Makita, Yoshihiko ; Yamada, Fumio
概要:
The simple total synthesis of the ergot alkaloids, (±)-norchanoclavine-I, (±)-chanoclavine-I, (±)-isochanoclavine-I, and
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(±)-agroclavine was achieved by a practical and common synthesis method. A new regio-selective oxidation of the Z-methyl group of the isoprenyl system with selenium dioxide is described.
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| 52.
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Somei, Masanori ; Yamada, Fumio ; Yamamura, Gaku
概要:
A simple synthetic method for 5H-pyrido[4, 3-b]indole (γ-carboline) derivatives having a methoxycarbonyl group at the 4-
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position was developed based on 1-hydroxyindole chemistry. By applying the method, various 3-substituted metyl 5H-pyrido[4, 3-b]indole-4-carboxylates and 2-substituted methyl 2, 3-dihydro-3-oxo-5H-pyrido[4, 3-b]indole-4-carboxylates were prepared.
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| 53.
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Somei, Masanori ; Yamada, Fumio ; Yamazaki, Yoshihisa ; Shinkura, Akiko
概要:
We developed a novel synthesis of 2-aminoindan derivatives, having a 2-methyl-1-propenyl group at the 1-position and oxygen functional groups in the benzene ring, in 8 or 9 steps from vanillin.
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| 54.
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Somei, Masanori ; Yamada, Fumio
概要:
A convenient, short synthesis of (±)-6, 7-secoagroclavine is developed having a 36% overall yield, high regio-and stereo-selectivity, and using no protecting groups.
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| 55.
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Somei, Masanori ; Yamada, Fumio ; Naka, Katsumi
概要:
A new cross coupling reaction between tin compounds and thallium compounds is developed and its versatility is demonstrated by the convenient synthesis of various 4-substituted indoles.
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| 56.
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Somei, Masanori ; Yamada, Fumio ; Kurauchi, Takashi ; Nagahama, Yoshiyuki ; Hasegawa, Masakazu ; Yamada, Koji ; Teranishi, Sakiko ; Sato, Haruhiko ; Kaneko, Chikara
概要:
Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a),
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bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
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| 57.
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Yamada, Fumio ; Tamura, Mayumi ; Hasegawa, Atsuko ; Somei, Masanori
概要:
Psilocin analogs having either a formyl group (9—12) or a bromine atom (13—18) at the 5- or 7-position have been prepare
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d for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N, N-dimethyltryptamine (32, 34, 35) have also been established.
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| 58.
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Somei, Masanori ; Inoue, Satomi ; Tokutake, Shoichi ; Yamada, Fumio ; Kaneko, Chikara
概要:
Various 1-hydroxyindoles carrying a nitro, methoxycarbonyl, or benzyloxy group at the 4 position were prepared by the co
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ntrolled reduction of 6-substituted trans-β-dimethylamino-2-nitrostyrenes with either aqueous titanium (III) chloride or zinc in aqueous ammonium chloride. The stability of 4-substituted 1-hydroxyindoles decreased in the following order : 4-nitro-»4-methoxycarbonyl->4-benzyloxy-1-hydroxyindole. This result clearly indicates that an electron-withdrawing group at the 4-position can stabilize the 1-hydroxyindole structure. It was also found that 4-hydroxy-and 4-benzyloxy-indole were readily accessible by the reduction of 6-benzyloxy-2-nitrophenyl acetaldehyde. A unique route to 4-or 7-aminoindole from cinnoline is also described.
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| 59.
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Yamada, Fumio ; Makita, Yoshihiko ; Suzuki, Tomoko ; Somei, Masanori
概要:
The first synthesis of (±)-aurantioclavine by a convenient and practical five-step synthetic method, involving a new int
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ra-molecular cyclization of nitro-olefin, is achieved starting from 3-formylindole with a 31% overall yield without using any protective groups.
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| 60.
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Yamada, Fumio ; Makita, Yoshihiko ; Somei, Masanori
概要:
Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate
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, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 61.
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Sato, Masako ; Suzuki, Yoshiaki ; Yamada, Fumio ; Somei, Masanori
概要:
Various derivatives of (6R (*),6aR (*))-6-chloro-6a-hydroxy-5, 6,6a,12-tetrahydroindolo[2,3-a]carbazole-5-one (8) and 6-
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cyano-5- hydroxyindolo[2,3-a]-carbazole (9) are prepared. Preparations of (6R (*),6aR (*),11aR (*))-6-chloro-11a-cyano-6a-hydroxy- (11) and 12-substituted 6-(Z)-aminomethylidene-5,6,6a, 11,11a,12-hexahydroindolo[2,3-a] carbazole-5-ones (15) are also reported. © 2010 The Japan Institute of Heterocyclic Chemistry Received.
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| 62.
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-pos
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ition with various types of nucleophiles providing 2,3,6-trisubstituted indole derivatives. The reaction is applicable for the preparation of a novel pyrimido[1,2-a]indole derivative. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 63.
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Yamada, Fumio ; Fukui, Yoshikazu ; Iwaki, Takako ; Ogasawara, Sachiko ; Okigawa, Masaki ; Tanaka, Satomi ; Somei, Masanori
概要:
A simple and new method for the preparation of optically active methyl 3a-chloro-, 3a-bromo-, 3a-hydroxy-, and 3a-alkoxy
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-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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| 64.
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Somei, Masanori ; Sayama, Shinsuke ; Naka, Katsumi ; Shinmoto, Kotaro ; Yamada, Fumio
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />Abstract - Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally
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related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 65.
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Yamada, Fumio ; Kawanishi, Atsuko ; Tomita, Akiko ; Somei, Masanori
概要:
1-Hydroxy-2,3-dimethylindole (1) has been prepared for the first time. Under atmospheric oxygen, 1 was converted rapidly into 3-hydroxy-2,3-dimethyl- 3H-indole N-oxide (2). The structure was deduced, based on its products obtained
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by the reaction with Ac2O in pyridine and confirmed by X-ray single crystallographic analysis.
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| 66.
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授
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| 67.
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Yamada, Fumio ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />A novel reductive amino-cyclization method for the synthesis of azacycloalkanes is dev
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eloped. Its versatility is proved by the total syntheses of (±)-aurantioclavine (1), an ergot alkaloid, and (±)-lophocerine (2), a cactus alkaloid, as examples of azepane and piperidine skeletons, respectively. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 68.
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Yoshino, Katsumasa ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />X-Ray analyses of 1-hydroxyyohimbine derivatives clearly show the deviation of the N(1
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)-O bond from the indole molecular plane. This phenomenon supports our working hypothesis "bishomoallylic conjugation". The deviation is responsible for the unprecedented nucleophilic substitution reaction in 1-hydroxyindole chemistry and effected the synthesis of novel 7β-heteroarylyohimbine and 4aα-heteroaryl-1,2,3,4-tetrahydro-β-carboline derivatives from the corresponding 1-hydroxyindole derivatives. © 2008 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 69.
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Somei, Masanori ; Yamada, Fumio
概要:
A novel reductive amino-cyclization method for the synthesis of azacycloalkanes is developed. Its versatility is proved
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by the total syntheses of (±)-aurantioclavine (1), an ergot alkaloid, and (±)-lophocerine (2), a cactus alkaloid, as examples of azepane and piperidine skeletons, respectively. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 70.
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染井, 正徳 ; 山田, 文夫 ; Somei, Masanori ; Yamada, Fumio
概要:
1.インドロ[2,3-a]カルバゾール化合物群の研究<br />(1)インドリンから1-ヒドロキシインドールを合成する新反応を見出し,1-メトキシインドールへ誘導後2位をリチウム化し酸化カップリングして,2,2'-ビインドリル(1)を得る新
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手法を開拓した。<br />(2)インジゴを還元して,1,3-アセトキシ-2,2'ミビインドリル(2),1-アセチル-2,3-ジヒドロ-2,2'-ビインドリル(3)をそれぞれ1工程で,選択的に作り分ける独自の新反応を3種類見い出した。<br />(3)1,2,3のそれぞれを出発原料として,抗菌,抗ガン作用を持つ天然物,6-シアノ-5-メトキシインドロ[2,3-a]カルバゾール(4)に適用可能な5種類の新規全合成法を見出した。<br />(4)4に至る合成中間体から,様々な4の誘導体の合成が可能となった。<br />(5)N-グリコシル-2,2'-ビインドリル(5)の簡単な合成法を開拓し,本基質から,N-グリコシルインドロ[2,3-a]カルバゾール化合物群を得る新手法を見出した。<br />(6)5位に酸素官能基を有するインドロ[2,3-a]カルバゾール化合物群の簡便な新しい一般合成法を確立した。<br />2.インドロ[2,3-a]カルバゾール化合物研究の発端となった1-ヒドロキシおよび1-メトキシインドール化学の展開<br />(1)1-ヒドロキシインドール類はこれまで未知であった求核置換反応を5位で位置選択的に起こすという新事実を発見することが出来た。<br />(2)1-ヒドロキシおよび1-メトキシインドール類は,その構造に基づく特徴的な新反応を数多く起こし,新反応,新事実の宝庫であることが分かった。<br />(3)これまで全くその存在も知られていなかった,インドールの化学における独創的な,全く新しい領域への扉を開くことが出来,今後の進展は末広がりの状態となっている。 1. Study toward Indolo [2,3-α] carbazoles<br /> Important building blocks such as 2,2'-biindolyl, 3-acetoxy-2,2'-biindolyl, 1-acetyl-2,3-dihydro-2,2'-biindolyl were prepared by our own new reactions from industrially available chemical, indigo. Utilizing these compounds as starting materials, four short step total synthetic routes to an antibiotic, 6-cyano-5-methoxyindolo [2,3-α] carbazole, were developed.<br /> N-Glycosyl 2,2'-biindolyls were also prepared and found to be excellent substrates for producing N-glycosylindolo [2,3-α] carbazoles.<br /> Above methods are widely applicable for the syntheses of various kinds of indolo [2,3-α] carbazoles.<br />2. The Chemistry of 1-Hydroxyindoles<br /> 2,2'-Biindolyl was also prepared through oxidative coupling of lithium 1-methoxyindol-2-yl and converted to indolo [2,3-α] carbazoles which constituted the fifth synthetic route.<br /> 1-Methoxyindoles are prepared from 1-hydroxyindoles, which are new compounds in indole chemistry. The chemistry of 1-hydroxyindoles was widely examined and found to be rich in a lot of new findings that were not expected from thusfar known indole chemistry.<br /> A frontier in indole chemistry is now open.<br />研究課題/領域番号:10470466, 研究期間(年度):1998–2000, 研究成果報告書の一部を掲載(pp.1-22:研究成果報告書の概要, 本研究の背景および成果についての概説, pp.46-50,pp.51-54:第23回および第25回 反応と合成の進歩シンポジウム―ライフサイエンスを志向した理論、反応及び合成―講演要旨集の抜粋, 主催:日本薬学会)<br />出典：「創薬を指向したインドロカルバゾールを共通骨格とする抗ガン性天然物の短工程合成研究」研究成果報告書 課題番号10470466 (KAKEN：科学研究費助成事業データベース（国立情報学研究所）) 本文データは著者版報告書より作成
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| 71.
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山田, 文夫 ; Yamada, Fumio
概要:
金沢大学理工研究域<br />1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indole骨格の3a位に酸素側鎖を持つ天然物や関連したfurano[2,3-b]indole骨格を有する天然物が数多く知られている。こ
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れらの天然物は、アセチルコリンエステラーゼ阻害作用等の強い生理活性を示すことから多くの研究者により合成研究が活発におこなわれている。これらの天然物合成に役立つbuilding blocksとして、また痴呆症治療薬の新しい医薬品のリード化合物になる可能性のある化合物群として、3a位にハロゲンや酸素官能基を持つ光学活性8-methoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole誘導体を想定し、その合成研究を開始した。昨年度までの研究成果に基づき、本年度は、3a位にハロゲン、酸素官能基を有する光学活性methyl 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate誘導体の合成法を確立するために、Nb-acetyl-1-methoxy-L-tryptophan methyl ester(1)を基質として研究をおこない、以下の事実を明らかにした。1.昨年までの研究で、我々が見出した3a位への直接アルコキシ化反応を光学活性な1-methoxy体(1)に適用した。すなわち、1をMeOH中morpholine存在下、10倍モルのヨウ素と室温下反応すると(2S,3aS,8aS)-および(2S,3aR,8aR)-methyl 1-acetyl-3a-methoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylatesがそれぞれ6%,48%の収率で得られた。Isopropanolの場合には、(2S,3aS,8aS)体および(2S,3aR,8aR)体がそれぞれ6%,34%の収率で得られた。2.アセトニトリル中1-methoxy体(1)をNCSおよびNBSでハロゲン化すると、3a位に塩素原子を有する光学活性な(2S,3aS,8aS)体および(2S,3aR,8aR)体がそれぞれ42%,42%の収率で、3a位に臭素原子を持つ光学活性な(2S,3aS,8aS)体および(2S,3aR,8aR)体がそれぞれ8%,81%の収率で生成した。3.得られた3a-chloro体のジアステレオマーをそれぞれ、アセトニトリル-水混合溶媒中AgCNと反応させると、対応する光学活性な3a-hydroxyy体へと高収率で誘導することができた。4.得られた光学活性なジアステレオマーの構造は、^1H-NMRスペクトルおよびX線結晶構造解析法を用い決定できた。次年度は、1-methoxytryptophanのNb上の置換基およびベンゼン環上の置換基の反応に対する効果を検討する。同時に様々な誘導体を合成し薬理試験を実施する予定である。<br />研究課題/領域番号:17590086, 研究期間(年度):2006 – 2007<br />出典：「痴呆症治療薬の創造を意図したピロロ〔2,3-b〕インドール化合物群の合成展開研究」研究成果報告書 課題番号17590086（KAKEN：科学研究費助成事業データベース（国立情報学研究所））（https://kaken.nii.ac.jp/ja/grant/KAKENHI-PROJECT-17590086/)を加工して作成
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