Synthetic Studies on Lignans and Related Compounds. V. Regiospecificity in the Photocyclization of 2,3-Dibenzylidenebutyrolactones

スポンサーリンク

概要

• 論文の詳細を見る

• The photocyclization of 2,3-dibenzylidenebutyrolactones (5) was investigated in association with the possible biogenetic pathway to natural naphthalide lignans in which 1-phenyl-2,3-naphthalide types predominate over 4-phenyl-2,3-naphthalide ones. The butyrolactones (5) were prepared via Stobbe condensation of benzylidenesuccinates (6) followed by the selective reduction of the resulting half esters (7) to hydroxy acids (8) and subsequent lactonization. and their cis, cis-configuration was assigned on the basis of comparative proton magnetic resonance (^1H-NMR) data. Irradiation of 5 afforded selectively β-apolignans (11) of the 1-phenyl-2,3-naphthalide types irrespectively of the ring substituents, and none of the 4-phenyl-2,3-naphthalide types was formed in the reaction.

• 社団法人日本薬学会の論文
• 1977-10-25

著者

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 金井 健一

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  富山医薬大・薬

• 中村 健

  Faculty of Pharmaceutical Sciences, Osaka University

• 国 雪子

  Faculty of Pharmaceutical Sciences, Osaka University

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Osaka University

• 中村 健

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 国 雪子

  Faculty Of Pharmaceutical Sciences Osaka University

関連論文

• 新しい入試制度を体験して
• Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one
• 1,6-Dihydro-3 (2H)-pyridinones. II. Synthesis of 2-Azabicyclo [2. 2. 2] octanes by the Reaction of N-Substituted 1,6-Dihydro-3 (2H)-pyridinones with 1,3-Dicarbonyl Compounds
• 1,6-Dihydro-3 (2H)-pyridinones. I. Facile Synthesis of N-Substituted 1,6-Dihydro-3 (2H)-pyridinones
• 含窒素共役系の反応(第8報)Dimethyl Inidazole-4,5-dicarboxylateとAnetholeとの反応生成物の構造について
• 含窒素共役系の反応(第7報)N-CinnamylidenemethylamineとN-Methyl-maleimideとめ付加体について
• 含窒素共役系の反応(第6報)2,3-Diphenyl-5,6-dihydropyrazineとDiethyl FumarateまたはN-Methylmaleimideとの付加体の立体構造について
• Synthetic Studies on Anthracyclinones. XIII. Conversion of Bisanhydro-γ-rhodomycinone into Bisanhydrodaunomycinone
• Synthetic Studies on Anthracylinones. XI. Abnormal Products from Phenolic Compounds on Methylation with Dimethyl Sulfate in Tetrahydrofuran
• Anthracyclinone類の合成研究(第10報) : Methyl 2-(1-Acetoxy-3-oxobutyl)phenylacetateの合成
• Synthesis of Bisanhydrodaunomycinone
• The Preparation of Fused Ring α, β-Unsaturated Lactones using Lithium Ethoxyacetylide. Syntheses of Dihydroactinidiolide and Actinidiolide, and Partial Synthesis of Dihydrosecurinine
• 86 分子内アミノ環化反応を用いる効率的なアルカロイドのキラル合成(ポスター発表の部)
• Synthetic Studies on Lignans and Related Compounds. VIII. : Synthesis of Justicidin B and Diphyllin and of Taiwanin C and E from 2,3-Dibenzylidenebutyrolactones via β-Apolignans : A Chemical Model for Natural Co-occurrence of 4-Hydrogen-and 4-Hydroxy-1-ph
• Synthetic Studies on Lignans and Related Compounds. VII. : Synthesis of β-Apoplicatitoxin Trimethyl Ether
• Synthetic Studies on Lignans and Related Compounds. VI. Photochemical Rearrangement of β-Apolignans
• Synthetic Studies on Lignans and Related Compounds. V. Regiospecificity in the Photocyclization of 2,3-Dibenzylidenebutyrolactones
• Synthetic Studies on Lignans and Related Compounds. IV. Synthesis of Taiwanin C and E, and Justicidin D (Neojusticin A), E, and F (Taiwanin E Methyl Ether)
• 2(3H)- and 2(5H)-Furanones. IV. The Di-π-methane Rearrangement of 3,4-Bis(phenymethyl)-2(5H)-furanone
• 85 2-Alkyl-ω-azabicyclo[3.n.1]alkan-3-one類の位置選択的α開裂を利用したα,α'位シス置換ピペリジン及びピロリジンアルカロイドの合成(ポスター発表の部)
• Marine Natural Products. XXVI. Biologically Active Tridecapeptide Lactones from the Okinawan Marine Sponge Theonella swinhoei(Theonellidae).(2).Structures of Theonellapeptolides Ia, Ib, Ic, and Ie
• Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVII. : A Novel Interconversion between Bicyclo-[4.3.1]decane and Tricyclo[4.3.1.0]decane Systems via the Dual Mode of Aldol Cyclization of Bicyclo-[4.3.1]decane-3,8-dione
• Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVI. On the Selectivity in the Ring Enlargement of the Bicyclo[3.3.1]nonan-2-one System
• Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XV. : Ring Enlargement of Bicyclo[3.3.1]nonane-2,6-dione and Bicyclo[3.3.1]nonan-2-one; Revision of the Literature
• Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. IX. Photo-Irradiation of Bicyclo [3....1] alkan-3-one in Cyclohexane : A Selective Photo-Reduction with Predominance of endo-Hydrogenation
• 3-Hydroxypyrroles. III. Synthesis and Tautomerism of N-Alkyl-3-hydroxypyrroles
• Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. V. The Baeyer-Villiger Oxidation of Bicyclo [3. 3. 1] nonane-3,7-dione and Its Congeners
• Bicyclo [3. 3. 1]nonanes as Synthetic Intermediates. IV. Behavior of Bicyclo [3. n. 1] alkan-3-ones toward the Baeyer-Villiger Oxidation
• Octahydro-7 (1H)-quinolones. VII. A Stereoselective Synthesis of cis, trans-Decahydro-3H, 8H-benzo [i, j] quinolizine-3,8-dione
• 3-Hydroxypyrroles. II. The Reaction of 4,5-Unsubstituted Alkyl 3-Hydroxypyrrole-2-carboxylates with Some Electrophiles
• Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. III. The Baeyer-Villiger Oxidation of Some Bicycloalkyl Phenyl Ketones
• 10 リコポジウムアルカロイドの合成研究 : (±)-Anhydrolycodoline及び(±)-Lycopodineの全合成
• 79(P06) 新規ピペリドン型キラルビルディングブロックの創製とその天然物合成への応用(ポスター発表の部)
• 31 生体触媒を活用した汎用性キラル素子の創製と天然物合成への応用(口頭発表の部)
• 73 リパーゼを利用するキラルγ-ブチロラクトンの合成法の開発とその天然物合成への応用(ポスター発表の部)
• 50 不斉アミノ環化反応を利用する含窒素生物活性物質の合成(口頭発表の部)
• TOTAL SYNTHESIS OF (+)-MONOMORINE I VIA ASYMMETRIC α-KETONIC CLEAVAGE OF 8-AZABICYCLO[3.2.1]OCTAN-3-ONE
• Synthetic Studies on Anthracyclinones. XIV. On the Conformational Aspects of Ring A of Daunomycinone : A Model Study
• 29 6員環上アリル位2級アルコールの立体配座とアセテート則
• 26 Anthracyclinoneの合成
• Synthetic Studies on η-Pyrromycinone. V. Total Synthesis of η-Pyrromycinone
• Synthetic Studies on η-Pyrromycinone. IV. Conversion of 1,11-Dimethoxy-5(12H)-naphthacenones into 4,6-Dimethoxynaphthacenequinones by Chromium Trioxide Oxidation
• Synthetic Studies on η-Pyrromycinone. III. Intramolecular Cyclization of methyl 2-Ethyl-5-hydroxy-6-(2-carboxy-3,6-dimethoxybenzoyl)-1-naphthoate
• Synthetic Studies on η-Pyrromycinone II. Synthesis of Methyl 2-Ethyl-5-Hydroxy-1-naphthoate
• Synthetic Studies on Anthracyclinones. IX. Lithiation of N, N-Dimethylnaphthalenemethylamines and a New Synthetic Pathway to 2,3-Naphthalides
• Synthetic Studies on Lignans and Related Compounds. III. Structure and Synthesis of Diphyllin
• Synthetic Studies on Lignans and Related Compounds. II. Synthesis of 1-Hydroxy-3-hydroxymethyl-6,7-dimethoxy-4-(3,4-methylenedioxyphenyl)-2-naphthoic Acid γ-Lactone and Its Non-identity with Diphyllin
• Synthetic Studies on Lignans and Related Compounds. I. Synthesis of 1-Hydroxy-3-hydroxymethyl-4-(3,4-dimethoxyphenyl)-6,7-methylenedioxy-2-naphthoic Acid γ-Lactone
• 22 Diphyllinの構造と合成
• Local Cerebral Glucose Utilization in Rats with Decerebrate Rigidity and Effects of Centrally Acting Muscle Relaxants, Diazepam and Tizanidine
• 3-Hydroxypyrroles. I. A General Synthetic Route to 4,5-Unsubstituted Alkyl 3-Hydroxypyrrole-2-carboxylates
• Synthetic Studies on Anthracyclinones. XII. Synthesis of 8-Ethyl-1,6,11-trihydroxynaphthacenequinone
• Bicyclo [3. 3. 1] nonanes as Synthetic Intermediates. II. Synthesis of Bicyclo [3. n. 1] alkan-3-one via α, α'Annelation of Cycloalkanone
• Bicyclo [3.3.1] nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo [3.3.1] nonan-3-one
• Octahydro-7 (1H)-quinolones. IV. Construction of Decahydro-3H, 10H-benzo [i, j] quinolizine-3,10-dione Systems from cis-and trans-Octahydro-7 (1H)-quinolone
• Octahydro-7 (1H)-quinolones. III. cis-trans Isomerization of Octahydro-7 (1H)-quinolone Analogues
• Octahydro-7 (1H)-quinolones. II. A Stereoselective Synthesis of cis-Octahydro-7 (1H)-quinolone
• Octahydro-7 (1H)-quinolones. I. Stereochemistries of Catalytic Hydrogenation of 7-Hydroxyquinoline
• Synthesis of (±)-Hydroxysugiresinol (Sequirin B) Trimethyl Ether
• Synthetic Studies on the Lycopodium Alkaloids. III. Synthesis of a Key Intermediate, Ethyl Octahydro-4aβ-hydroxy-7β-methyl-10-oxo-1H-5,8α-propanoquinoline-1-carbamate, for the Lycopodium Alkaloids
• The Structures of Securinol B and C
• Synthetic Studies on Anthracyclinones. VIII. Synthesis of 4-Bromo-6-ethyl-1-naphthol
• Synthetic Studies on Anthracyclinones. VII. Synthesis of Bisanhydroaklavinone
• Synthetic Studies on Anthracyclinones. VI. The Friedel-Crafts Condensation between 3-Methoxyphthalic Anhydride and α-Naphthol Derivatives
• Synthesis of Bisanhydroaklavinone
• 2-Acetyl-1-naphthoic and 2-Acetyl-3,4-dihydro-1-naphthoic Acid.
• Conversion of Methyl 2-Ethyl-6,11-dihydro-6,11-dioxo-5,7,10-trimethoxy-1-naphthacenecarboxylate into η-Pyrromycinone
• Synthesis of Methyl 2-Ethyl-6,11-dioxo-5,7,10-trimethoxy-6,11-dihydro-1-naphthacenecarboxylate (η-Pyrromycinone Trimethyl Ether)

もっと見る 閉じる

スポンサーリンク