41 ピクロトキサン型セスキテルペン,コリアミルチンの合成研究
スポンサーリンク
概要
- 論文の詳細を見る
Starting from protoanemonin (7), synthetic investigation of dl-coriamyrtin (1) was undertaken. The 1,6 adduct (6) from (7) and (8) was subjected to react with isopropenylmagnesium bromide-CuI to afford the compound (9) and (10). All trials to convert these compounds to the (4) type compounds possessing the correct stereo-chemistries for the present synthesis were unfruitful. On the other hand, a series of reactions of (27) from (6), acidic methanolysis, isopropenylmagnesium bromide-CuI and acidic hydrolysis, gave stereoselectively the compound (4) in four steps. The compound (4) was derived to the lactone (3) by the mixed-anhydride method and treatment of (3) with NBS gave the bromo-ether (31). After several unfruitful trials for introducing the C_1 unit to the carbonyl group at C_9 of (31), (32) and (33), the prolactone (34) was treated with Ph_3P=CH_2 and Me_2S=CH_2 to give (37) and (36), respectively. The subsequent conversions of (36) and (37) to the natural product, however, were unsuccessful. The Wittig reaction of the saturated ketone (34) under the reaction condition reported by Conia gave the exomethylene compound (47), which was transformed to the bromo-ether (49). Oxidation of (49) by the Sharpless methods gave a single product (51), in good yield. Dehydration of (51), followed by epoxidation afforded a diastereomeric mixture of diepoxides (53). Separation and definite identification of the synthetic product with bromo-coriamyrtin are in progress.
- 天然有機化合物討論会の論文
- 1981-09-10
著者
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内山 文昭
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
Faculty Of Pharmaceutical Sciences Kyoto University
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田中 圭
静岡県大 薬
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犬伏 康夫
京大薬学科
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犬伏 康夫
Faculty Of Pharmaceutical Sciences Kyoto University
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坂元 清志
Faculty of Pharmaceutical Sciences, Kyoto University
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池田 隆春
Faculty of Pharmaceutical Sciences, Kyoto University
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田中 圭
京大薬
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内山 文昭
京大薬
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浅田 與
京大薬
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池田 隆春
京大薬
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坂元 清志
京大薬
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田中 圭
京都大学薬学部
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浅田 與
Faculty Of Pharmaceutical Sciences Kyoto University
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坂元 清志
Faculty Of Pharmaceutical Sciences Kyoto University
-
池田 隆春
Faculty Of Pharmaceutical Sciences Kyoto University
関連論文
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- Chiral Piperazines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes
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- Studies on Pilocereine and Related Compounds. III. Synthesis of 2,2', 3-Trimethoxydiphenyl Ether-4', 5- and -4', 6-dicarboxaldehyde.
- Studies on Pilocereine and Related Compounds. II. Cleavage of O-Methylisopilocereine by Metallic Potassium in Liquid Ammonia.
- 4.Pilocereineの異性体Isopilocereineの構造について
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- exo-Adduct Predominance in the Diels-Alder Reaction of Novel 1,3-Bis-(trimethylsiloxy) cyclohexa-1,3-dienes with Acrylonitrile
- 56 dl-Pumiliotoxin Cの立体選択的合成
- Regioselective Intramolecular Aldol Condensation by Using Excess Morpholine-Camphoric Acid
- Total Syntheses of the Lycopodium Alkaloids (±)-Fawcettimine and (±)-8-Deoxyserratinine
- Synthetic Studies on 8-Deoxyserratinine Type Alkaloids. Selective Cyclization of the 1,2-Cyclohexanediacetaldehyde Derivative by Intramolecular Aldol Condensation
- 78 8-Deoxyserratinine系lycopodium塩基の合成研究
- The Stereochemistry of Diels-Alder Adduct of 2-(3-Acetoxypropyl)-5-methylcyclohex-2-en-1-one with Butadiene
- 60 2,5-DialkylcyclohexenoneのDiels-Alder反応を用いる2,3の天然物の合成研究
- REDOX POTENTIAL OF OLIGONUCLEOTIDE LINKED TO 5-DEAZAFLAVIN COENZYME MODEL. DETECTION OF HYBRID FORMATION BY CYCLIC VOLTAMMOMETRY
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- 天然物合成から (有機合成の考え方--研究テ-マはどのように生まれ育ったか) -- (有機合成の発想・展開・展望--われわれの体験から)
- 41 ピクロトキサン型セスキテルペン,コリアミルチンの合成研究
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- 24 (±)Hasubanonineの合成
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- 41 Serratene diol系triterpenoidのC-CH_3基帰属におけるNMR shift reagentの応用
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- The Substituent Effect on the Addition Course of the Diels-Alder Reaction of 2-Methyl-5-substituted-1,4-benzoquinones with Butadiene
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