Meisenheimer Rearrangement of Azetopyridoindoles. VI. Synthesis of 12-Carbaeudistomin and Related Compounds

スポンサーリンク

概要

• 論文の詳細を見る

• For structure-activity relationship investigation of eudistomins 1,12-carbaeudistomin 3,its 1,10-trans isomer 4,and 11,12-didehydro-12-carbaeudistomin 5 have been synthesized. The [2,3]-Meisenheimer rearrangement of the corresponding N-oxide of the 2-vinylazetopyridoindole 12a bearing a benzenesulfonyl group as a protective group of the indole nitrogen atom afforded the oxazepino ester 14,which was easily isomerized to 20a. Compounds 3 and 4 were synthesized from 14 and 20a, respectively, according to the following reaction sequences [hydrogenation of the double bond (Pd-C/H_2), desulfonylation (Mg in MeOH), hydrolysis (AlBr_3-EtSH), and Curtius rearrangement (a mixed anhydride method using NaN_3), followed by debenzylation (Pd-C/H_2]. The Curtius reaction of the carboxylic acid 27 using DPPA gave the carbamate 29,which was subjected to debenzylation (AlBr_3-EtSH) followed by desulfonylation (LiAlH_4) to afford 5. Evaluation of anti-influenza virus activities of the amino compounds 3,4,and 5 revealed that 12-carbaeudistomin 3 possesses a specific activity against influenza virus B.

• 公益社団法人日本薬学会の論文
• 1994-03-15

著者

• 春沢 信哉

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  大阪薬科大学

• 米田 龍司

  Agroscience Research Laboratories Sankyo Co. Ltd.

• Sakamoto Y

  Alfresa Pharma Co.

• 坂本 靖彦

  (present Address)research Laboratories Nippon Shoji Kaisha Ltd.

• 松本 宏美

  Osaka University Of Pharmaceutical Sciences

• 栗原 拓史

  Osaka College Of Pharmacy

• 川端 夏来

  Osaka University of Pharmaceutical Sciences

関連論文

• Synthetic Studies of (±)-Lysergic Acid and Related Compounds(Organic,Chemical)
• Studies on Indenopyridine Derivatives and Related Compounds. VI. : Synthesis adn Stereochemistry of Ethyl 9.9-Dimethyl-1,2,3,9a-tetrahydro-9H-indeno[2,1-b]pyridine-3-carboxylate as a Possible Intermediate for the Total Synthesis of Lysergic Acid
• A NEW SYNTHESIS OF (±)-LYSERGIC ACID
• Improved Synthesis of 5'-Deoxy-5'-adenosineacetic Acid
• Thermal Elimination of Carbonyl Sulfide from O-Aryl Thionocarbonates of Pyrrolidine-, Piperidine-, and Tetrahydrothiophene-2-ethanol
• Novel Transformation of Azabicyclothionocarbonate to Azaspirolactone
• Molecular Conformations of Aminophenylimidazoles Exhibiting Antiulcer Activities
• Synthesis of Novel 4(5)-(5-Aminotetrahydropyran-2-yl)imidazole Derivatives and Their in Vivo Release of Neuronal Histamine Measured by Brain Microdialysis
• Studies on Ergot Alkaloids and Related Compounds. XIV. Syntheses of N-Alkyl-4-methyl-2,3,4,4a, 5,6-hexahydrobenzo [f] quinoline-2-carboxamides and Stereochemistry of Diethyl 4-Methyl-1-oxo-1,2,3,4,4a, 5,6,10b-octahydrobenzo [f] quinoline-2,2-dicarboxylate
• Studies on Ergot Alkaloids and Related Compounds. XIII. syntheses and Stereochemistries of 4-Methyl-1,2,3,-4,4a, 5,6,10b-octahydrobenzo[f]quinoline-2-carboxylic Acids
• Studies on 1,4-Benzothiazines. II. Acetylation of 2,3-Dihydro-3-imino-4H-1,4-benzothiazine
• Studies on 1,4-Benzothiazines. I. Synthesis of 2,3-Dihydro-3-imino-4H-1,4-benzothiazines and Acetylation of the N-Methyl Derivative
• ラット扁桃核キンドリング発作に対する各種ヒスタミンH3受容体拮抗薬の効果
• キノリン-3-酢酸誘導体の合成とその生理活性
• Meisenheimer Rearrangement of Azetopyridoindoles. VII. Ring Expansion of 2-Phenylhexahydroazeto[1', 2' : 1,2]pyrido[3,4-b]indoles by Oxidation with m-Chloroperbenzoic Acid
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. VII. On the Formation of 8-Membered Thionocarbonates as the Intermediates
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. VI. Regioselective Wohl-Ziegler Bromination of 10-Membered Thiolcarbonates
• Chemistry of Tetrahydro-1,3-oxazin-2-one : New Method for the Synthesis of Indoloquinolizidine Derivatives
• MEISENHEIMER REARRANGEMENT OF 2-ETHENYL-1,4,5,10b-TETRAHYDRO-2H-AZETOPYRIDO[3,4-b__-]INDOLE N-OXIDES : NEW ROUTE TO THE 12(S)CARBA-EUDISTOMIN SKELETON
• 亜リン酸トリエチルによる3,6-Dichloro-4-(o-nitrophenyl)pyridazineの閉環反応について
• アミノアゾール類の亜硝酸との反応に関する研究(第2報) : 5-ハロゲノイソオキサゾールについて
• アミノアゾール類の亜硝酸との反応に関する研究(第1報)
• Reductive Cyclization of o-Nitrobenzylideneacetylacetone Analogues
• Effects of Constituents from the Bark of Magnolia obovata on Nitric Oxide Production in Lipopolysaccharide-Activated Macrophages
• Studies on Indenopyridine Derivatives and Related Compounds. III. Stereochemistry of 1-Substituted 4,9-Dihydroxy-9-phenyl-1,2,3,4,4a, 9a-hexahydro-9H-indeno [2,1-b] pyridines
• Reaction of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. V. X-Ray Determination of the Molecular Structure of a Reaction Product of 6,7-Diethoxycarbonylpyrazolo [1,5-α] pyrimidine-3-carbonitrile with N-Methylindole
• New Farnesane-Type Sesquiterpenes, Hedychiols A and B 8,9-Diacetate, and Inhibitors of Degranulation in RBL-2H3 Cells from the Rhizome of Hedychium coronarium
• 含フッ素スルホンアミド誘導体の合成
• オキサゾール, イソオキサゾール類のハロゲン化について
• オルトニトロアニリンのSchiemann反応における転位について
• フェノール誘導体のクロルメチル化について
• Synthesis of 1-Triazolyl-4-trimethylsilyl-2-butanol and 1-Triazolyl-5-trimethylsilyl-2-pentanol Derivatives and an Investigation of Their Fungicidal Activities
• Synthesis and Systemic Fungicidal Activity of Silicon-Containing Azole Derivatives
• A New Method for the Preparation of 2-Hydroxymethyl-3-quinolinecarboxylic Acid Lactone Derivatives
• Reactions of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. IV. Some Reactions of 1,4-Dihydrocyclopent [b] indoles
• THE REACTION OF 1,4-DIHYDROCYCLOPENT [b] INDOLES WITH DIMETHYL ACETYLENEDICARBOXYLATE
• Reaction of 3-[3-(2-Nitrophenyl)-2-propenylidene]-2,4-pentanedione with Hydroxylamine Hydrochloride. Formation of a 2-Chloromethyleneindolin-3-one
• Reactions of Pyrazolo [1,5-a] pyrimidine Derivatives with Nucleophiles. III. Nucleophilic Addition to 6,7-Bis (ethoxycarbonyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile in the Presence of Triethyloxonium Fluoroborate
• Synthesis and Reactions of Ethyl 6-Acetyl-2,3-diphenylimidazo [1,2-a] pyrimidine-5-carboxylate and Related Compounds
• SYNTHESIS AND X-RAY CRYSTAL STRUCTURE DETERMINATION OF 1,4-DIHYDROCYCLOPENT [b] INDOLES
• Ring Transformations of 6H-Cyclopropa [e] pyrazolo [1,5-a] pyrimidine. III. Synthesis and X-Ray Crystal Structure Determination of a 1-Pyrazol-3-ylpyrrole-2-carboxylic Acid
• Reactions of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. I. Nucleophilic Addition to 6,7-Dicarbethoxypyrazolo [1,5-α]-pyrimidine-3-carbonitrile in the Presence of Boron Trifluoride Etherate
• Ring Transformations of 6H-Cyclopropa[5a, 6a]pyrazolo[1,5-a]pyrimidine. II. Reaction of 5a-Acetyl-6a-carbethoxy-5a, 6a-dihydro-6H-cyclopropa[5a, 6a]pyrazolo[1,5-a]pyrimidine-3-carbonitriles with N-Methylaniline
• Reactions of Ethyl 3-Ethoxymethylene-2,4-dioxovalerate and Ethyl Ethoxymethyleneoxaloacetate with Indole Analogs
• Studies on Ergot Alkaloids and Related Compounds. XII. Syntheses of Ethyl 4-Methyl-2,3,4,4α, 5,6-hexahydrobenzo[f]quinoline-2-carboxylate and its Dihydro Derivative
• Synthesis of (±)-trans- or cis-(5-Aminomethyltetrahydrofuranyl)imidazole by Mitsunobu Cyclization : Synthetic Studies toward Novel Histamine H_3 or H_4-Ligands
• Efficient and β-Stereoselective Synthesis of 4(5)-Methyl-5(4)-(5-amino-5-deoxy-β-D-ribofuranosyl)imidazole and Related Compounds Exhibiting Antiulcer Activity
• Meisenheimer Rearrangement of Azetopyridoindoles. VIII. Synthesis and Antiviral Activities of 12-Carbaeudistomin Analogs
• Formation of 2-Acetyl-3-hydroxy-5-phenylmaleimide from Ethyl 3-Ethoxy-methylene-2,4-dioxovalerate and Phenylhydroxylamine
• Studies on Ergot Alkaloids and Related Compounds. XVI. On the So-called Bohlmann Absorption of 2,4-Disubstituted Octahydrobenzo [f] quinoline Derivatives
• Studies on Ergot Alkaloids and Related Compounds. XV. Reductions of cis- and trans-4-Methyl-2-methylen-3-oxo-1,2,3,4,4a, 5,6,10b-octahydrobenzo [f] quinolines and Preparation of trans-syn-2,4-Dimethyl-1,2,3,4,4a, 5,6,10b-octahydrobenzo-[f] quinoline
• REACTION OF METHYL VINYL KETONE CYANOHYDRIN PHOSPHATE WITH AROMATIC COMPOUNDS
• Meisenheimer Rearrangement of Azetopyridoindoles. V. Synthesis of 9-Methyl-12-carbaeudistomin and Related Compounds
• 2-Acetyl-3-hydroxymaleimide誘導体の反応性(第1報)アミン類との反応について
• 1,4-and 1,7-Addition Reactions of 4-(Substituted benzylidene)-3,5-dimethylisopyrazoles
• Reaction of 4-(o-Nitrobenzylidene)-3,5-dimethylisopyrazole with Acyl Chlorides
• Studies on Indenopyridine Derivatives and Related Compounds. I. Syntheses and Stereochemistries of 1-Substituted 1,2,3,4,4a, 9a-Hexahydro-4-hydroxy-9H-indeno [2,1-b] pyridines and Related Compounds
• A NEW SYNTHESIS OF BIARYLS
• イミダゾール C- ヌクレオシド誘導体の合成研究とヒスタミン H_3 および H_4 リガンドヘの応用
• Meisenheimer Rearrangement of Azetopyridoindoles. III. Synthesis of 3,6-Epoxyhexahydroazocino[5,4-b]indoles
• Efficient Synthesis of trans- or cis-4(5)-(5-Aminomethyltetrahydrofuran-2-yl)imidazoles via Diazafulvene Intermediates: Synthetic Approach toward Human Histamine H_4-Ligands
• Antiinflammatory Principles and Three New Labdane-Type Diterpenes, Hedychilactones A, B, and C, from the Rhizome of Hedychium coronarium Koeng
• Meisenheimer Rearrangement of Azetopyridoindoles. VI. Synthesis of 12-Carbaeudistomin and Related Compounds
• Application of Cyanophosphates in Organic Synthesis. Reactivity of α-Cyano-α-diethylphosphonooxy Anions(Organic,Chemical)
• Allylic Rearrangement of Cyanophosphates. III. : Reaction of Acyclic Enone Cyanophosphates
• Studies on Isopyrazole Derivatives and Related Compounds. I. Structure of Condensation Product of Nitrobenzylideneacetylacetone with Hydrazine Dihydrochloride
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. IV. Relatioship between Ring Size of Cyclic Thionocarbonates and Geometry of Created Double Bond in Medium- and Large-Membered Thiolcarbonates
• Reductive Deoxygenation of α, β-Unsaturated Ketones via Cyanophosphates by Lithium in Liquid Ammonia
• Synthesis and Cycloaddition Reaction of 2-Cyano-3-indoleacetonitriles
• CYANOPHOSPHORYLATION OF KETONES AND ALDEHYDES USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• New Route to 1-(5-Imidazolyl)ribofuranoid Glycals from Ribofuranosyl Chloride and 5-Lithio-imidazole
• RECYCLISATION OF 2-OXOTETRAHYDRO-1,3-OXAZINES ACCOMPANIED BY DECARBOXYLATION : A CONVENIENT SYNTHESIS OF TETRAHYDROPYRIDINE, QUINOLIZIDINE, AND INDOLIZIDINE SKELETONS
• Studies on the [2,3]-Meisenheimer Rearrangement of 2-Vinylazetidine N-Oxides
• 中環状チオノカルボナートの[3,3]シグマトロピー転位を経由した環拡大反応
• シアノヒドリンΟ-ジエチルリン酸エステル類の有機合成への応用
• 奨励賞受賞 浦田秀仁氏の業績
• A New Synthesis of Allenic Nitriles from Ynones via Cyano Phosphates
• NEW ROUTE TO (Z)-ALLYLIC SULFIDES VIA A 10-MEMBERED THIOLCARBONATE
• Allylic Rearrangement of Cyanophosphate. II. Synthesis of β-Cyano-α, β-unsaturated Ketones
• ALLYLIC REARRANGEMENT OF α, β-UNSATURATED KETONE-DIETHYL PHOSPHOROCYANIDATE ADDUCTS

もっと見る 閉じる

スポンサーリンク