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| 1.
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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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| 2.
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Somei, Masanori ; Hayashi, Hiroyuki ; Ohmoto, Shinobu
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 />Indigo was converted to 2,2′-bisindole by the direct reduction with zinc in ace
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tic acid and acetic anhydride under argon or hydrogen atmosphere. Reduction with tin and iron afforded 3-acetoxy-2,2′-bisindole predominantly. Useful building blocks such as 1-acetyl-2,3-dihydro-, 3-acetoxy-3′-acetyl-, and 3-acetoxy-1,3′-diacetyl-2,2′-bisindoles were also produced depending on metal and reaction conditions.
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| 3.
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Somei, Masanori ; Kodama, Atsushi
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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| 4.
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Somei, Masanori ; Kobayashi, Tetsuya
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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| 5.
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Somei, Masanori ; Hayashi, Hiroyuki ; Izumi, Tohru ; Ohmoto, Shinobu
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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| 6.
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Hayashi, Hiroyuki ; Ohmoto, Shinobu ; 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 />The first simple total syntheses of 6-cyano-5-methoxy- (1a) and -12-methylindolo[2,3-a]carba
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zolc (1b) are attained from indigo (2) in only five and six steps, respectively. Preparations of 5-hydroxy- (13), 5-bromoindolo[2,3-a]carbazole (14), and a novel spiro compound (7) are also included.
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| 7.
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Kaneko, Chikara ; Fujii, Harue ; Kawai, Shinji ; Hashiba, Kazuhiko ; Karasawa, Yoshio ; Wakai, Masue ; Hayashi, Reiko ; Somei, Masanori
概要:
Irradiation (≥300 nm) of methyl 2-phenyl-3, 1-benzoxazepine-5-carboxylate in an alcohol afforded the Z-isomer of methyl
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3-alkoxy-2-(2-benzamidophenyl)-acrylate as the major addition product. In contrast, thermal reaction of the oxazepine with a primary alcohol in the presence of triethylamine led to the exclusive formation of the corresponding E-isomer. The same kinds of Michael addition products were also obtained stereoselectively from 3, 1-benzoxazepines having an acetyl group at the 5-position under these conditions. The interrelation between the stereoisomers obtained from the oxazepine and an alcohol under these two conditions was established by photochemical equilibration, and the stereochemistry of the two isomers was determined by proton magnetic resonance spectroscopy. An explanation is proposed for the observed stereoselectivities in the two kinds (photochemical and thermal) of reactions.
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| 8.
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Kaneko, Chikara ; Naito, Toshihiko ; Hashiba, Marimi ; Fujii, Harue ; Somei, Masanori
概要:
Two alkaloids, 1-methyl-4-(3-methylbut-2-enyloxy)-2-quinolone (revenine : IIc) and 4-methoxy-1-methyl-2-quinolone (IIa), were synthesized by means of a photochemical rearrangement reaction of the corresponding
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4-alkoxy-2-methylquinoline 1-oxide (Ic and Ia), which were conveniently prepared from 4-chloro-2-methylquinoline 1-oxide (XVII), which in turn is readily obtainable from 2-methylquinoline 1-oxide via the 4-nitrated compound (XVIII). The mechanism of the photo-rearrangement reaction of 4-alkoxy-2-methylquinoline 1-oxides (Ia-d) in methanol is discussed.
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| 9.
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Hayashi, Hiroyuki ; Suzuki, Yoshiaki ; 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 />Starting from indigo, simple synthetic methods for 6-cyano-5-methoxy- 12-methyl
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indolo[2,3-a]carbazole and novel 6-aminoindolo[2,3-a]thiazolo-[5,4- c]carbazoles are achieved using only conventional reagents.
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| 10.
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Somei, Masanori ; Ohnishi, Hiroyuki
概要:
The first synthesis of (±)-paniculidine B is achieved from 2-nitrotoluene in seven steps with an overall yield of 16%.
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