Total Synthesis of Chelerythrine, a Benzo[c]phenanthridine Alkaloid
スポンサーリンク
概要
- 論文の詳細を見る
By taking advantage of our novel synthetic methods involving CsF-mediated Claisen rearrangement of an aryl propargyl ether to a 2-methylbenzolfuran and oxidative cleavage of the furan ring to a salicylaldehyde, total synthesis of chelerythrine, a benzo[c]phenanthridine alkaloid, was accomplished via the common intermediate (5) prepared through the two routes shown in Chart 3.
- 社団法人日本薬学会の論文
- 1992-08-25
著者
-
鈴木 雅博
Hanno Research Center Chemistry Lab. Taiho Pharmaceutical Co. Ltd.
-
石井 永
Faculty of Pharmaceutical Sciences, Chiba University
-
石川 勉
Faculty of Pharmaceutical Sciences, Chiba University
-
武田 直
Faculty of Pharmaceutical Sciences, Chiba University
-
鈴木 雅博
Faculty of Pharmaceutical Sciences, Chiba University
-
原山 尚
Faculty of Pharmaceutical Sciences, Chiba University
-
石川 勉
千葉大薬
-
石川 勉
千葉大院薬
-
原山 尚
Faculty Of Pharmaceutical Sciences Kyoto University
-
石井 永
Faculty Of Pharmaceutical Sciences Chiba University
-
Ishii H
Faculty Of Pharmaceutical Sciences Tokushima Bunri University
-
武田 直
Faculty Of Pharmaceutical Sciences Chiba University
関連論文
- Piperazinealkanol Ester Derivatives of Indomethacin as Dual Inhibitors of 5-Lipoxygenase and Cyclooxygenase
- Total Synthesis of Chelerythrine, a Benzo[c]phenanthridine Alkaloid
- Total Synthesis of Lemaireocereine
- Cesium Fluoride-Mediated Claisen Rearrangement of Aryl Propargyl Ether. Exclusive Formation of 2-Methylarylfuran and Its Availability as a Masked Salicylaldehyde
- 22 フッ化セシウム存在下でのアリールプロパルギルエーテルのクライゼン転位 : 2-メチルアリールフランの生成とそのイソキノリンアルカロイド合成への応用(ポスター発表の部)
- CESIUM FLUORIDE-MEDIATED CLAISEN REARRANGEMENT OF ARYL PROPARGYL ETHER AND ITS APPLICATION TO THE SYNTHESIS OF CHELERYTHRINE
- Synthesis of 5-Carbon-Substituted 1-β-D-Ribofuranosylimidazole-4-carboxamides via Lithiation of a Primary Carboxamide(Organic,Chemical)
- Synthetic Studies on dl-Aspterric Acid, a Carotane-Type Sesquiterpene. II. Synthesis of dl-Aspterric Acid(Organic,Chemical)
- BIOSYNTHESIS IN VITRO OF 2-(3-AMINO-3-CARBOXYPROPYL)-ISOXAZOLIN-5-ONE, THE NEUROTOXIC AMINO ACID IN LATHYRUS ODORATUS
- BIOSYNTHESIS OF β-(ISOXAZOLIN-5-ON-2-YL)ALANINE, THE PRECURSOR OF THE NEUROTOXIC AMINO ACID β-n-OXALYL-L-α, β-DIAMINOPROPIONIC ACID
- 96(P-26) タイ産植物Pueraria mirificaを起原とする健康食品"プエラリア"の品質管理 : 指標イソフラボンKwakhurinの全合成及び簡易HPLC検査法の開発(ポスター発表の部)
- 84(P-16) ホモケリドニンの立体選択的全合成(ポスター発表の部)
- 9 回春秘薬「プエラリア」の活性成分(口頭発表の部)
- 110(P42) 抗HIV-1活性Calophyllumクマリン合成へのアプローチ(ポスター発表の部)
- アスピリンはどうして効くの, またそのルーツは?(どうしてそうなるの 4)
- 抗HIV-1活性Calophyllumクマリンの化学
- Studies on the Chemical Constituents of Xanthoxylum nitidum (ROXB.)D. C. (Fagara nitida ROXB.). III. The Chemical Constituents of the Wood
- Synthesis of Toddacoumaquinone, a Coumarin-Naphthoquinone Dimer, and Its Antiviral Activities
- Concise Syntheses of the Oxo Derivatives of Benzo[c]phenanthridine Bases by N-Deformylated Cyclization Based on Vilsmeier-Haack Reaction
- Studies on the Chemical Constituents of Xanthoxylum nitidum (ROXB). D. C. (Fagara nitida ROXB.). II. Examination of the Chemical Constituents by Membrane Filtration : Identification of Magnoflorine, a Water-Soluble Quaternacy Aporphine Alkaloid
- Toddalosin, a New Biscoumarin, from Toddalia asiatica (L.) LAM.(T. aculeate PERS.)
- Synthetic Studies on Naturally Occurring Coumarins. II. Synthesis of 6,7-Dimethoxy- and 7,8-Dimethoxy-5-[(E)-3-oxo-1-butenyl]coumarins
- An Efficient Method for Preparing gem-Dimethylcyclopropanes from gem-Dibromocyclopropanes(Organic,Chemical)
- Reaction of 8,8-DibromobicycJo[5.1.0]octanes with Higher-Order Organocuprates(Organic,Chemical)
- AN EFFICIENT METHOD FOR PREPARING GEM-DIMETHYLCYCLOPLOPANES FROM GEM-DIBROMOCYCLOPROPANES
- CHEMILUMINESCENT REACTIONS OF "UNMODIFIED" FLAVINS
- Alkoxycarbonylmethylation of(3R, 10bS)-3-Phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline
- Fischer Indolization and Its Related Compounds. XIX. Syntheses of Ethyl 4-Methoxy- and Ethyl 5-Methoxy-1-phenyl-3H-benz [e] indole-2-carboxylates
- REVISION OF STRUCTURE OF A NEW COUMARIN ISOLATED FROM Artemisia carviforia Wall
- On the Repair of Thymine and Thymidine Bromohydrins : A Possible New Model for the Damage and Repair of Nucleic Acids
- Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
- 高次有機銅試薬を用いるgem-ジブロモシクロプロパン体のアルキル化反応について
- Fischer Indolization of Ethyl Pyruvate 2-[2-(Trifluoromethyl)phenyl]-phenylhydrazone and New Insight into the Mechanism of the Goldberg Reaction. (Fischer Indolization and Its Related Compounds. XXVI)
- Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II. : Synthesis of Bromo- and Methoxycarbonylcoumarins
- A Convenient Preparation of Salicylaldehydes from 2-Methylbenzofurans by Ozonolysis
- Synthetic Studies on Naturally Occurring Coumarins. I. A Convenient Synthesis of 5,8-Dimethoxy- and 7,8-Dimethoxycoumarins
- TODDACOUMAQUINONE, A UNIQUE COUMARIN-NAPHTHOQUINONE DIMER, FROM TODDALIA ASIATICA (L.) LAM. (T. ACULEATA PERS.)
- A CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN
- Re-examination of the Synthesis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinylphenyl)iso carbostyril
- Studies on the Chemical Constituents of Rutaceous Plants. L. Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (2). Preparation of 2-Aryl-1-tetralone Derivatives
- Studies on the Chemical Constituents of Rutaceous Plants. XLIX. Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (1). Preparation of Various 2,4-Bisaryl-4-oxobutyronitriles and 2,4-Bisaryl-4-oxobu
- Chelirubine
- THE CHEMICAL REPAIR REACTION OF THYMINE AND THYMIDINE DIOL DERIVATIVES, MODELS OF OXIDATIVELY DAMAGED NUCLEIC ACIDS, BY TRIVALENT PHOSPHORUS COMPOUNDS
- Studies on the Chemical Constituents of Rutaceous Plants. LX. Development of a Versatile Method for Syntheses of the Antitumor Benzo [c] phenanthridine Alkaloids. (9). Efficient Syntheses and Antitumor Activities of Nitidine and Related Nonphenolic Benzo
- O-Methyldeoxopunjabine, a Secobisbenzylisoquinoline Alkaloid Bearing an Aryl Methyl Group, and Three Other Secobisbenzylisoquinoline Alkaloids, O-Methylpunjabine, Secocepharanthine, and Dihydrosecocepharanthine, from Stephania Sasakii
- Studies on the Chemical Constituents of Rutaceous Plants. LI. Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (3). Detailed Examination of the Synthesis of 2-Aryl-1-formamido-1,2,3,4-tetrahydrona
- 14 セファランチンを中心としたビスベンジルイソキノリン型アルカロイドの化学における新展開
- Studies on the Alkaloids of Menispermaceous Plants. CCLXXV. Syntheses of [methylenedioxy-^C] Cepharanthine and a Related Compound
- Studies on the Chemical Constituents of Rutaceous Plants. LV. The Development of a Versatile Method for the Synthesis of Antitumor Active Benzo [c] phenanthridine Alkaloids. (5). A New Method for Quaternization of the Benzo [c] phenanthridine Nucleus
- Studies on the Chemical Constituents of Rutaceous Plants. LIV. The Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (4). Limitation of Bischler-napieralski Cyclization and Detailed Examination of
- Structural Establishment of Chelilutine Due to the Chemical Correlation with Nitidine and Isoarnottianamide
- Fischer Indolization and Its Related Compounds. XVIII. Formation of Four Unexpected Angular Benz [e] indoles on Fischer Indolization of Ethyl Phenylpyruvate 2-[(1,4-Dimethoxy-2-naphthyl) hydrazone]
- 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
- The Stereochemistry of Diels-Alder Adduct of 2-(3-Acetoxypropyl)-5-methylcyclohex-2-en-1-one with Butadiene
- Abnormal Fischer Indolization and Its Related Compounds. XII. Synthesis of 3,6'-Biindole
- Fischer Indolization and Its Related Compounds. VIII. Formation of 4-Aminoindole Derivatives on the Fischer Indolization of 2-Methoxyphenylhydrazone Derivatives
- Fischer Indolization and Its Related Compounds. VI. Effect of Reagents and Substituent of the ortho-Substituted Phenylhydrazone on Abnormal Fischer Indolization
- Development of "Abnormal" Fischer Indolization to Syntheses of 3,6'-Biindole and Its Derivatives
- 医薬品の特許
- Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone
- Fischer Indolization and Its Related Compounds. XXIII. Fischer Indolization of Ethyl Pyruvate 2-(2,6-Dimethoxyphenyl)phenylhydrazone
- Sanguirubine and Sanguilutine
- Structure of Serratanidine
- 有機天然化合物の化学は、今……
- ミカン科植物アルカロイド研究(第18報) : カラスザンショウXanthoxylum ailanthoides SIEB. et ZUCC.(Fagara ailanthoides(SIEB.et ZUCC.) ENGL.)のアルカロイド その2 根部のアルカロイド
- Studies on Lysergic Acid Diethylamide and Related Compounds. IX. Microbial Transformation of Amides Related to Lysergic Acid Diethylamide by Streptomyces roseochromogenes
- Studies on Lysergic Acid Diethylamide and Related Compounds. VII. Microbial Transformation of Lysergic Acid Diethylamide and Related Compounds
- Studies on the Chemical Constituents of Rutaceous Plants. XLVI. The Chemical Constituents of Xanthoxylum integrifoliolum (MERR.) MERR. (Fagara integrifoliola MERR.) II. Structural Establishment of Integriquinolone, a New Phenolic Quinolone
- ONE-POT UNSYMMETRICAL DOUBLE SUBSTITUTION OF 8,8-DIBROMOBICYCLO[5.1.0]OCTANE AND ITS STEREOCEHMISTRY
- PHOTOCHEMISTRY OF 2-(3,4,5-TRIMETHOXYPHENYL)-4-(3,4-METHYLENEDIOXYPHENYL)-4-OXO-2-BUTENONITRILE (β-CYANOCHALCONE) : ANOMALOUS DIMERIZATION THROUGH ISOMERIZATION IN THE SOLID STATE
- AILANTHOIDINE, A NOVEL BENZO[C]PHENANTHRIDINE ALKALOID WITH A CYANOPYRIDINE PENDANT, FROM A XANTHOXYLUM SPECIES
- New Indole Trimer
- 薬学の野球戦士達
- Stereo-Structures of Reaction Products of dl-1,3-Dimethylthymine Epoxide with Amines and L-Amino Acid Ethyl Esters(Organic,Chemical)
- Oxidation of Pyrimidine Base Derivatives with m-Chloroperbenzoic Acid
- OXIDATION OF 1,3-DIMETHYL DERIVATIVES OF PYRIMIDINE BASES WITH m-CHLOROPERBENZOIC ACID
- Fischer Indolization and Its Related Compounds. V. Indolization of Ethyl Pyruvate 2-Methoxyphenylhydrazone and Its N-Methyl Derivative with Protic Acids. Unpredictable Products and the Mechanism
- Abnormal Fischer Indolization and Its Related Compounds. XXII. : Fischer Indolization of Ethyl Pyruvate 2-(2-Chloro- and 2,6-Dichlorophynyl)methylhydrazones
- 日本薬学会奨励賞受賞 竹内義雄氏の業績
- 製薬企業発行の情報誌
- Studies on the Chemical Constituents of Rutaceous Plants. LXIV. Structural Establishment of Oxyterihanine, a Phenolic Benzo[c]phenanthridone Alkaloid. Syntheses of Phenolic Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Related Compou
- Studies on the Chemical Constituents of Rutaceous Plants. LVI. The Development of a Versatile Method for the Synthesis of Antitumor-Active Benzo [c] phenanthridine Alkaloids. (6). Limitation of the Dyke Synthetic Pathway for Benzo [c] phenanthridine Alkal
- The Plane Structure of Serratinine
- Serratinine ; A Novel Skeletal Lycopodium Alkaloid
- Oxidation of 6-Methyl-2-phenylbenzofuran with Chromic Acid under Various Conditions. An Abnormal Dimeric Oxidation Product of the Benzofuran Derivative. Studies on the Heterocyclic Quinones. V
- Studies on the Chemical Constituents of Rutaceous Plants. XXXVI. Synthesis of Ethyl Isodecarine
- EFFECTIVE TOTAL SYNTHESIS OF FAGARONINE : ANTILEUKEMIC PHENOLIC BENZO[c]PHENANTHRIDINE ALKALOID
- Studies on Lysergic Acid Diethylamide and Related Compounds. V. Syntheses of Dihydrolysergic Acid Diethylamides and Related Compounds
- Total Synthesis of the Lycopodium Alkaloid dl-Serratinine
- The Stereochemistry of Diels-Alder Adduct of 5-Methyl-2-cyclohexene-1-one with Butadiene
- Selective Cyclization of the 1,2-Cyclohexanediacetaldehyde Derivatives through the Intramolecular Aldol Condensation Reaction
- The Substituent Effect on the Addition Course of the Diels-Alder Reaction of 2-Methyl-5-substituted-1,4-benzoquinones with Butadiene
- The Structures of Two Lycopodium Alkaloids, Lycothunine and Lycophlegmarine, and the Configuration of the C_3-C_4 Bond of Fawcettimine and Fawcettidine
- (+)-Peucedanol Methyl Ether from Hippomarathrum cristatum, Umbelliferae
- Structural Establishment of Arnocoumarin and Arnottiacoumarin due to Chemical Modification of Marmesin and Rutaretin Methyl Ether
- Xanthoarnol : A New Dihydrofuranocoumarin
- Arnottinin : Structural Establishment by Chemical Correlation with Osthenol
- TODDALENONE : A NEW COUMARIN FROM TODDALIA ASIATICA (T. ACULEATA) STRUCTURAL ESTABLISHMENT BASED ON THE CHEMICAL CONVERSION OF LIMETTIN INTO TODDALENONE