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Saito, Miho ; Matsuo, Jun-ichi ; Uchiyama, Masahiko ; Ishibashi, 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 />金沢大学薬学部<br />Treatment of N-(2-arylcyclohex-l-enyl)-α-(methylthio)acetamide with NCS underwe
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nt cyclization to give 3a-arylhexahydroindol-2-one, which was stereoselectively converted into trans-3a-aryloctahydroindole. © 2006 The Japan Institute of Heterocyclic Chemistry.
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| 2.
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Takeuchi, Kosuke ; Ishita, Atsuko ; Matsuo, Jun-ichi ; Ishibashi, 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 />A radical cascade involving 6-endo cyclization of aryl radicals generated from N-acryloyl-N-
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(1-methylethenyl)-9-bromophenanthren-10-ylmethylamines, followed by 5-endo-trig cyclization of the resulting α-amidoyl radicals afforded phenanthroindolizidines bearing a methyl substituent at the angular C13a position. 2,3,6-Trimethoxy derivative was synthesized by using this method, but its spectral data were not in accord with those of literature values reported for hypoestestatin 1. Further synthetic study toward hypoestestatin 1 is demonstrated. © 2007 Elsevier Ltd. All rights reserved.
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| 3.
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石橋, 弘行 ; 田村, 修 ; Ishibashi, Hiroyuki ; Tamura, Osamu
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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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Matsuo, Jun-ichi ; Tanaki, Yumi ; Ishibashi, Hiroyuki
概要:
金沢大学医薬保健研究域薬学系<br />Indolenines were generated at -78 °C from 3-benzylic or 3-allylic indoles by dehydrogenation with N-
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tert-butylbenzenesulfinimidoyl chloride, and a carbon-carbon bond was formed at -78 °C in a one-pot manner by treating these indolenines with various carbon nucleophiles such as active methylene compounds or organocuprates. © 2008 Elsevier Ltd. All rights reserved.
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| 5.
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Matsuo, Jun-ichi ; Okano, Masahiko ; Takeuchi, Kosuke ; Tanaka, Hiroyuki ; Ishibashi, 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 />金沢大学薬学部<br />Enantiomerically pure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine
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was synthesized by the asymmetric reduction of a β-enamino ester formed from benzyl 2-oxocyclohexanecarboxylate and (R)-phenylethylamine, followed by hydrogenolysis, phthaloylation, and the Curtius rearrangement. © 2007.
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| 6.
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論文
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Matsuo, Jun-ichi ; Tanaki, Yumi ; Ishibashi, Hiroyuki
概要:
金沢大学医薬保健研究域薬学系<br />Indolenines were generated at -78 °C from 3-benzylic or 3-allylic indoles by dehydrogenation with N-
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tert-butylbenzenesulfinimidoyl chloride, and a carbon-carbon bond was formed at -78 °C in a one-pot manner by treating these indolenines with various carbon nucleophiles such as active methylene compounds or organocuprates. © 2008 Elsevier Ltd. All rights reserved.
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| 7.
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Matsuo, Jun-ichi ; Kawai, Hiroki ; Ishibashi, 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 />金沢大学薬学部<br />金沢大学医学部附属病院薬剤部<br />A carbon-carbon bond was formed at the β-position of cyclic
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ketones in a one-pot manner by oxidation with N-tert-butylbenzenesulfinimidoyl chloride, followed by the reaction of malonic acid esters or potassium cyanide. © 2007 Elsevier Ltd. All rights reserved.
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| 8.
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Tamura, Osamu ; Morita, Nobuyoshi ; Takano, Yuu ; Fukui, Kenji ; Okamoto, Iwao ; Huang, Xin ; Tsutsumi, Yoshiyuki ; Ishibashi, 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 />金沢大学薬学部<br />Ethyl glyoxylate O-tert-butyldimethylsilyloxime, on treatment with various alke
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nes in the presence of BF3·OEt2, generated a C-ethoxycarbonyl N-boranonitrone intermediate, which underwent intermolecular cycloaddition to afford 3-(ethoxycarbonyl)isoxazolidines in moderate to high yields. © Georg Thieme Verlag Stuttgart.
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| 9.
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Saito, Miho ; Matsuo, Jun-ichi ; Ishibashi, 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 />金沢大学薬学部<br />Treatment of N-(2-arylcyclohex-1-en-1-yl)-α-(methylthio)acetamides with N-chlor
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osuccinimide (NCS) gave 3a-aryl-2,3,3a,4,5,6-hexahydro-3-(methylthio)indol-2-ones. Desulfurization of the cyclization products followed by a catalytic hydrogenation of the resulting hexahydroindol-2-ones gave predominantly or exclusively trans-fused octahydroindol-2-ones. On the other hand, reduction of the desulfurization products with Et3SiH in CF3CO2H exclusively provided cis-fused octahydroindol-2-ones. A chiral induction of N-[2-(3,4-dimethoxy)phenylcyclohex-1-en-1-yl]-α-(methylthio)acetamide having an (R)-1-(1-naphthyl)ethyl group on the nitrogen atom led to the synthesis of (-)-mesembrane and (-)-trans-mesembrane. © 2007 Elsevier Ltd. All rights reserved.
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| 10.
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Taniguchi, Tsuyoshi ; Yonei, Daigo ; Sasaki, Masamichi ; Tamura, Osamu ; Ishibashi, 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 />The effect of positional change of the carbonyl group of enamides on Bu3SnH-mediated alkyl r
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adical cyclization leading to five-, six-, seven-, and eight-membered nitrogen-containing heterocycles was examined. A 5-exo cyclization is generally preferred over a 6-endo ring closure in systems having an alkyl radical center on the enamide-acyl side chain, whereas enamides having an alkyl radical center opposite to the acyl side chain predominantly gave 6-endo cyclization products. These results suggest that the exo or endo selectivity of radical cyclization onto the alkenic bond of enamides can be controlled by positional change of the carbonyl group. For an understanding of these selectivities, heat of formation for each transition state was calculated. 6-endo-Selective radical cyclization was applied to the radical cascade, enabling a concise synthesis of a cylindricine skeleton. A 7- or 8-endo alkyl radical cyclization, however, predominated over a corresponding 6- or 7-exo ring closure regardless of the positional change of the carbonyl group of enamides. © 2008 Elsevier Ltd. All rights reserved.
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