[2+2] Photocycloaddition Reaction of 5-Arylfuran-2,3-diones to Trimethylsilyloxyethylenes

スポンサーリンク

概要

• 論文の詳細を見る

• The photocycloaddition reaction of 5-phenylfuran-2,3-dione (1a) to 2-trimethylsilyloxybutadiene proceeded in a [2s+2s] manner with high regio- and stereo-selectivities to give a 2-oxabicyclo[3.2.0]heptane-3,4-dione 2 with 7-endo-OTMS-7-exo-vinyl stereochemistry. 5-Arylfuran-2,3-diones (1a-e) on similar photocycloaddition with 1-phenyl-1-trimethylsilyloxyethylene gave the corresponding 7-aryl derivatives 3a-e with the same regio- and stereo-chemistries in good yields. This stereochemical result of O-endo selectivity is consistent with the prediction obtained from the stereo-selection rule proposed for the enone-olefin photocycloaddition reaction. The reaction provides an efficient method for the synthesis of poly-functionalized cyclobutane derivatives.

• 公益社団法人日本薬学会の論文
• 1997-04-15

著者

• Kiuchi Fumiyuki

  Faculty of Pharmacy, Keio University

• TSUDA YOSHISUKE

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• Kiuchi F

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Kikuchi F

  Faculty Of Pharmaceutical Sciences Kanazawa University:(present Address)graduate School Of Pharmaceu

• Kikuchi F

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Kiuchi Fumiyuki

  Faculty Of Pharmaceutical Sciences Kanazawa University

• SANO Takehiro

  Showa College of Pharmaceutical Sciences

• KOSEKI Nobuyuki

  Showa College of Pharmaceutical Sciences

• SAITOH Toshiaki

  Showa College of Pharmaceutical Sciences

• HORIGUCHI Yoshie

  Showa College of Pharmaceutical Sciences

• TODA Jun

  Showa College of Pharmaceutical Sciences

• Kiuchi Fumiyuki

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Kiuchi F

  Kanazawa Univ. Kanazawa Jpn

• Toda J

  Showa Coll. Pharmaceutical Sci. Tokyo Jpn

• Tsuda Yoshisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Tsuda Y

  Faculty Of Pharmaceutical Sciences And High Technology Research Center Kobe Gakuin University

• Horiguchi Y

  Showa Pharmaceutical University

• Koseki N

  Tokyo Metropolitan Geriatric Center Tokyo Jpn

関連論文

• In Vitro Leishmanicidal Activity of Benzophenanthridine Alkaloids from Bocconia pearcei and Related Compounds
• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Glycosphingolipids from the Parasite Schistosoma mansoni
• Anthelmintic Effect of the Embelia ribes Decoction and Embelin Derivatives on Trichuris muris in Mice
• Trichuris muris : The Anthelmintic Effect of Mebendazole in Mice is Dependent upon the Pre-treatment with Steroids
• Mobility Inhibition and Nematocidal Activity of Asarone and Related Phenylpropanoids on Second-Stage Larvae of Toxocara canis
• A Tetrazorium Dye (MTT) Assay for Testing Larval Viability Using Second-Stage Larvae of Toxocara canis
• Nematocidal Activity of Turmeric : Synergistic Action of Curcuminoids
• 105(P-46) キノン型ジテルペンの抗トリパノソーマ作用機構(ポスター発表の部)
• 107(P-62) 食品に由来する薬物相互作用物質の化学(ポスター発表の部)
• 58(P19) 神経成長因子産生促進作用を持つケロウジ由来ジテルペノイド類の構造(ポスター発表の部)
• 大麻種子の2,3,5-Triphenyl-2H-tetrazolium Chloride (TTC)による発芽能力鑑定法
• 90(P04) β-エリスロイジンの合成研究(ポスター発表の部)
• ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
• REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
• Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
• Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
• Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
• Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
• Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
• Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
• Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
• Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
• Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
• Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
• Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (4). Oxidation of Furan Ring of D-Furanoerythrinans with N-Bromoacetamide
• Tropane Alkaloid Production and Shoot Regeneration in Hairy and Adventitious Root Cultures of Duboisia myoporoides-D. leichhardtii Hybrid(Pharmacognosy)
• 日本薬局方収載のTLCによる生薬の確認試験について(1)1-ブタノール/水/酢酸(100)混液を展開溶媒とする確認試験
• Dioxopyrrolines. XLIII. : Diels-Alder Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione with Butadienes : Synthesis of Polyfunctionalized Hydroindoles
• A New Leishmanicidal Saponin from Brunfelsia grandiflora
• Two New Morphinane Alkaloids from Stephania cepharantha HAYATA (Menispermanceae)
• Synthesis of Erythrina and Related Alkaloids. XXX. Photochemical Approach. (1). Synthesis of Key Intermediates to Erythrina Alkaloids by Intermolecular [2+2] Photocycloaddition Followed by 1,3-Shift
• Dioxopyrroline. L. Skeletal Rearrangements of 7-Vinyl-7-trimethylsilyloxy-5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones under Thermal, Basic, and Acidic Conditions
• Dioxopyrrolines. XLVII. : Thermal Rearrangements of 7-Vinyl Derivatives of 1-Aryl-5-ethoxy-carbonyl-2-azabicyclo[3.2.0]heptane-3,4-diones and Their Imidates
• Synthesis of Erythrina and Related Alkaloids. XVI. Diels-Alder Approach: Total Synthesis of dl-Erysotrine, dl-Erythraline, dl-Erysotramidine, dl-8-Oxoerythraline and Their 3-Epimers(Organic,Chemical)
• 26 ホモエリスリナアルカロイド,(±)schelhammericine,(±)3-epischelhammericineの全合成
• TOTAL SYNTHESIS OF THE HOMOERYTHRINAN ALKALOIDS, SCHELHAMMERICINE AND 3-EPISCHELHAMMERICINE
• Dioxopyrrolines. XLIV. : Thermal 1,3-Shift of 2-Azabicyclo[3.2.0]hept-2-ene Ring System : A New Entry to 3,4-Dihydropyridines and 2-Azanorborn-2-enes
• Dioxopyrrolines.XLII. : Mechanism of 7-Epimerization Reaction of 7-Substituted 5-Ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones
• Dioxopyrrolines. XXXV. Synthesis of 2H-Azepin-2-ones (2-Azatropones)
• Effects of Long-Chain Fatty Acids and Fatty Alcohols on the Growth of Streptococcus mutans(Biological)
• Lycopodium植物トリテルペノイドの化学分類学的研究
• Cytotoxic Principles of a Bangladeshi Crude Drug, Akond Mul (Roots of Calotropis gigantea L.)
• Localization and contents of paradisins, the most potent CYP3A4 inhibitors, in grapefruit Citrus paradisii and grapefruit juice
• STUDIES ON BIOLOGICALLY ACTIVE COMPOUNDS CONTAINED IN CHINESE MEDICINAL PLANTS USED AGAINST THE STAGNATION OF DISORDERED BLOOD
• Synthesis and Nematocidal Activity of Diarylnonanoids Related to Malabaricones
• Synthesis and Nematocidal Activity of Aralkyl- and Aralkenylamides Related to Piperamide on Second-Stage Larvae of Toxocara canis
• [2+2] Photocycloaddition Reaction of 5-Arylfuran-2,3-diones to Trimethylsilyloxyethylenes
• Dioxopyrrolines. LXI. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-Dienes : Competitive Occurrence of Normal and Hetero Diels-Alder Reaction and Claisen Rearrangement of the Hetero Diels-Alder Product
• Total Synthesis of Homoerythrinan Alkaloids, Schelhammericine and 3-Epischelhammericine
• Dioxopyrrolines. XLIX. Synthesis of Azatropolones via Photocycloaddition of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones to Acetylenes and Ethylenes
• Dioxopyrrolines. XLVIII. : Regioselective Formation of Hydroindoles via Photochemical and Thermal Cycloaddition Reactions of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-dione with Isoprene
• Dioxopyrrolines. XLVI. : [2+2] Photocycloaddition of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Six-Membered Cycloolefins : Effect of Ring Size on Stereochemical Pathways
• Dixopyrrolines. XLV. : [2+2] photocycloaddition of 4-Ethoxycarbonyl-5-aryl-1H-pyrrole-2,3-dione to Cyclopentene Derivatives : Formation of Dihydropyridones
• Dioxopyrrolines. XLI. : X-Ray Crystallographic Determination of the Stereochemistry of an Azatricyclo[5.3.0.0^]decane Derivative Obtained by Photocycloaddition of Cyclopentadiene to 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione
• Dioxopyrrolines. XL. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Dihydrofurans. Formation of a 2,4-Dioxa-10-azatricyclo[6.3.0.0^]undecane Ring System(Organic,Chemical)
• Dioxopyrrolines. XXXVII. Stereochemical Pathways of Dioxopyrroline-Olefin Pbotocycloaddition. Stereochemical Selection Rule for the Photocycloaddition of Enone-Olefin Pairs(Organic,Chemical)
• Dioxopyrrolines. XXXVI. [2+2] photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assignment of the Photocycloadducts(Organic,Chemical)
• Dioxopyrrolines. XXIX. Solvolytic Behavior of 3-Ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-diones in Protic Solvents
• DNA Profiling of Acorus calamus Chemotypes Differing in Essential Oil Composition
• Acacia concinna Saponins. II. Structures of Monoterpenoid Glycosides in the Alkaline Hydrolysate of the Saponin Fraction
• Acacia concinna Saponins. I. Structures of Prosapogenols, Concinnosides A-F, Isolated from the Alkaline Hydrolysate of the Highly Polar Saponin Fraction
• Alkaloidal Constituents of the Leaves of Stephania cepharantha Cultivated in Japan : Structure of Cephasugine, a New Morphinane Alkaloid
• Alkaloidal Constituents of the Tubers of Stephania cepharantha Cultivated in Japan : Structure of 3,4-Dehydrocycleanine, a New Bisbenzylisoquinoline Alkaloid
• Martefragin A, a Novel Indole alkaloid Isolated from Red Alga, Inhibits Lipid Peroxidation
• A Synthesis of 3-Phenyl-1, 2, 3, 4-tetrahydroisoquinoline and 2-Phenyl-1, 2, 4, 5-tetrahydro-3H-3-benzazepine via Pummerer-Type Cyclization : Enhancing Effect of Boron Trifluoride Diethyl Etherate on the Cyclization
• A Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines via Pummerer-Type Cyclization of N-(2-Arylethyl)-N-(2-phenylsulfinylethyl)formamides
• A Synthesis of Chiral 1,1,3-Trisubstituted l,2,3,4-Tetrahydro-β-carbolines by the Pictet-Spengler Reaction of Tryptophan and Ketones: Conversion of (1R,3S)-Diastereomers into Their (1S,3S)-Counterparts by Scission of the C(1)-N(2) Bond
• A Convenient Synthesis of 1, 1-Disubstituted 1, 2, 3, 4-Tetrahydroisoquinolines via Pictet-Spengler Reaction Using Titanium(IV)Isopropoxide and Acetic-Formic Anhydride
• Chemical Transformation of Embelin through Dimerization during Preparation of a Decoction
• A New Diterpene Glycoside from Rabdosia Rubescens
• Dimerization of 2,5-Dihydroxybenzoquinones in Water
• Studies on Nepalese Crude Drugs. XXV. Phenolic Constituents of the Leaves of Didymocarpus leucocalyx C. B. CLARKE (Gesneriaceae)
• Studies toward Total Synthesis of Non-Aromatic Erythrinan Alkaloids. 7. Synthesis of Cocculolidine Skeleton
• A Synthesis of Heteroaromatic Analogues of 1-Methyl-1,2,3,4-tetrahydroisoquinoline Using the Pummerer-Type Cyclization Reaction : Observation of Tandem Cyclization Reaction
• Super Acid-Induced Pummerer-Type Cyclization Reaction : Improvement in the Synthesis of Chiral 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinolines
• Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile : Selective Construction of 1, 4-Benzothiazine and Indole Ring Systems
• Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl)propionamides
• A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome
• [2+2] Photocycloaddition Reaction of 5-Phenyl-1H-furan-2,3-dione to Phenylethylene
• A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl]formamide
• 脳内アミン,1-メチルテトラヒドロイソキノリンのパーキンソン病治療薬としての可能性
• A Synthesis of Mono- and Dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer Reaction : Effects of Methoxyl Groups on Intramolecular Cyclization
• General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids (1) : Synthesis of a Cycloerythrinan, as a Key Intermediate to Erythrina Alkaloids, by Pummerer-Type Reaction
• Determination of Ring Conformation in 1-Benzyl-1,2,3,4-tetrahydroisoquinolines and a New Synthesis of the Chiral Compounds
• An Improved Synthesis of 1,2,3,4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl)methyl-2-(phenylsulfinyl)ethylamine by Pummerer Reaction
• Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring : Formation of cis-Arranged Cyclic Thiolcarbonates
• Thio-Sugars. I. Radical-Promoted Thione-Thiol Rearrangement of Cyclic Thionocarbonates : Synthesis of 5-Thioglucose
• STEREOSELECTIVE SYNTHESIS OF AN ALKENOID-TYPE ERYTHRINAN ALKALOID, (±)-ERYTHRATIDINE
• Synthesis of Homoerythrinan Alkaloids of 1(2)-Alkene and 1,6-Diene Types : Total Synthesis of Comosine, Dihydroschelhammeridine, Schelhammeridine, and 3-Epischelhammeridine
• Oxidative Decarboxylation of Arylacetic Acids with Manganese(III)Acetate
• Chemistry of Oxo-Sugars. IV. Isomerization of 4-Oxoglycosides in a Pyridine Solution
• Thermal Addition Reaction of Aroylketenes with Cyclic Enol Ethers
• Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes : Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity
• Chemistry of Oxo-Sugars. III. Transformations of 2- and 3-Oxoglycosides in a Pyridine Solution
• Genetic and chemical comparison of Boi (Sinomeni Caulis et Rhizoma) and Seifuto (Caulis Sinomenii)
• エリスリナおよび関連アルカロイドの合成
• Synthesis of 2,3,4,5-Tetrahydro-1H-2-benzazepines via Pummerer-Type Cyclization of N-Arylmethyl-N-(3-phenylsulfinylpropyl)formamides
• Dioxopyrrolines. LX. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione to Olefins : An Inverse-Electron-Demand Hetero Diels-Alder Reaction
• Alkaloidal Constituents of Vines of Stephania cepharantha(Natural Medicine Note)
• ジオキソピロリンを利用した種々の含窒素複素環化合物の合成

もっと見る 閉じる

スポンサーリンク