19 モンタニン型アルカロイド、(±)-モンタニン、(±)-コクシニンの全合成(口頭発表の部)

スポンサーリンク

概要

• 論文の詳細を見る

• A first total synthesis of montanine-type alkaloids, (±)-montanine(1), (±)-coccinine(2), and (±)-pancracine(3) was accomplished as follows. Olefin diacetate (11) was prepared in several steps starting from anhydride(6) via tosylamide(10a). Stereoselective hydroboration-oxidation of 11 gave an alcohol(12) in a sole product, which was converted to 18 in several steps. Treatment of 18 with vitride^[○!R] in boilig xylene gave 5,11-methanomorphanthridine(19) in good yield. DIBAL reduction of 19 afforded 20a, which would be a potential key compound for synthesis of montanine-type alkaloids. Actually, 20a was converted to (±)-coccinine(2) in 5 steps. On the other hand, (±)-montanine(1) and (±)-pancracine(3) were synthesized through 27a, obtained by stereoselective chlorophenylselenylation of 26a under ultrasonication, which was derived from 20a in two steps.

• 天然有機化合物討論会の論文
• 1991-09-07

著者

• 星野 修

  東京理科大学薬学部

• 飯高 洋一

  Nishi-tokyo Science University

• 石崎 幸

  東京理科大薬

• 飯高 洋一

  School Of Medicine Teikyo University

• 飯高 洋一

  西東京大・理工

• 飯高 洋一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 飯高 洋一

  西東京科学大学理工学部

• 石崎 幸

  東京理科大学薬学部

• 星野 修

  東京理科大学 薬学部 薬化学教室

• 星野 修

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

関連論文

• Chemistry of Tremorogenic Metabolites. II. Structure Determination of Fumitremorgin B, a Tremorogenic Metabolite from Aspergillus fumigatus
• The Structure of Paeoniflorigenone, A New Monoterpene isolated from Paeoniae Radix
• 8 Carbazomycin類抗生物質の単離,構造および生合成
• Synthesis of 1,2,3-Triazine N-Oxides
• THE STRUCTURE OF 1,2,3-TRIAZINE
• ADDITION REACTION OF 1,2,3-TRIAZINE 2-IMINES WITH DIMETHYL ACETYLENEDICARBOXYLATE
• Studies on Tetrahydroisoquinolines. XXV. A Synthesis of 4-Aryl-1,2,3,4-tetrahydroisoquinolines ; Total Synthesis of (±)-Cherylline
• 8-クロロモルフィナンジエノンおよび8-クロロホモモルフィナンジエノンの合成 (生物活性物質)
• Studies on Tetrahydroisoquinolines. XII. An Alternative Synthesis of (±)-Bracteoline, (±)-Isoboldine, (±)-N-Methyllaurotetanine, and Their Related Aporphines
• Studies on Tetrahydroisoquinolines. X. A Stereospecific Synthesis of (±)-Cataline
• 振動を利用したユーイング装置によるヤング率の測定
• 3p-ZC-14 振動を利用したユーイング装置によるヤング率の測定
• Chetracin A and Chaetocins B and C, Three New Epipolythiodioxo-piperazines from Chaetomium spp.
• FISSOLDHIMINE, A NOVEL SKELETON ALKALOID FROM FISSISTIGMA OLDHAMII
• Biologically Active Constituents of Magnolia salicifolia : Inhibitors of Induced Histamine Release from Rat Mast Cells
• 58 セレチウムアルカロイドの合成研究
• 94(PB3-5) ビス(ナフト-γ-ピロン)系マイコトキシンの研究(ポスター発表の部)
• 21 ヒガンバナ科アルカロイド、(±)-リコリンの合成(口頭発表の部)
• 71 多重標識化合物の生合成研究への応用
• Synthetic Studies on Marasmane and iso-Marasmane Derivatives
• Studies on Tetrahydroisoquinolines. XXVI. : A Biomimetic Synthesis of 5-Oxygenated 1,2,3,4-Tetrahydroisoquinolines
• The Absolute Configuration of Curcumalactone(Pharmacognosy,Chemical)
• Antitumor Activity of Shikonin, Alkannin and Their Derivatives. II. X-Ray Analysis of Cyclo-alkannin Leucoacetate, Tautomerism of Alkannin and Cyclo-alkannin and Antitumor Activity of Alkannin Derivatives
• 2p-NR-9 32素子MCDDSの性能
• 2p-NR-8 32素子MCSSDの開発
• Studies on Metal Complexes of Isocytosine Derivatives : The Crystal Structures of Mercury(II) and Nickel(II) Complexes of 2-Hydrazino-4-hydroxy-6-methylpyrimidine
• Studies on Metal Complexes of Isocytosine Derivatives : The Molecular Structures of Platinum(II)and Platinum(IV)Complexes of 2-Hydrazino-4-hydroxy-6-methylpyrimidine
• Absolute Configurations of Chaetochromin A and Related Bis(naphtho-γ-pyrone) Mold Metabolites(Organic,Chemical)
• より魅力的な薬学教育を(入試制度と薬学教育)
• 2p-N-8 多素子SSDシステムとその特性
• 1p-U-2 一次元SSD(PSSD)の開発(III)
• シンクロトロン放射X線 (〔応用物理〕創刊50周年記念特集号) -- (放射線検出器への要求と期待)
• Inhibition of Prostaglandin Biosynthesis by 4-O-Methylcryptochlorophaeic Acid ; : Synthesis of Monomeric Arylcarboxylic Acids for Inhibitory Activity Testing and X-Ray Analysis of 4-O-Methylcryptochlorophaeic Acid
• タンパク質と核酸の基本構造パラメーターを求める簡単な X 線回折実習
• Ca2+依存性の制御タンパク質トロポニンCとカルモデュリンの立体構造 (1985年の化学-9-)
• THE ABSOLUTE CONFIGURATION AND CONFORMATION OF NEOCURDIONE
• 19 モンタニン型アルカロイド、(±)-モンタニン、(±)-コクシニンの全合成(口頭発表の部)
• Studies on Tetrahydroisoquinolines. XXX. A Synthesis of Mixed Tetrahydroisoquinoline Dimers via p-Quinol Acetates
• Studies on Tetrahydroisoquinolines. XXIII. Reactions of (±)-7-Acetoxy-7-methoxy-1-(3,4-dimethoxy-or 3,4-methylenedioxybenzyl)-2-methyl-6-oxo-Δ^-hexahydroisoquinoline (o-Quinol Acetate)
• Studies on Tetrahydroisoquinolines. XXI. A Synthesis of (±)-1-Hydroxy-2-methoxyhomoproaporphine and Stereochemistry of 4-Oxygenated 1,2,3,4-Tetrahydroisoquinolines
• 77 リコリン関連化合物の合成研究
• Constituents of Torilis scabra D.C. II
• 99(P20) ラジカル反応を利用する(+)-リコリンの合成研究(ポスター発表の部)
• Hongconin, a New Naphthalene Derivative from Hong-Cong, the Rhizome of Eleutherine ameicana MERR. et HEYNE(Iridaceae)
• 88 ラジカル反応を利用したモンタニン型アルカロイドの形式的全合成(ポスター発表の部)
• 新しい5-HT_受容体拮抗薬ナンテニンと受容体との相互作用の受容体結合実験およびモレキュラーモデリングによる解析
• RENEWED STUDIES ON THE STRUCTURE OF DIDYMIC ACID
• Structures of Torilolide and Oxytorilolide; Two Novel Germacranolides from Torilis japonica (HOUTT.) DC.
• A Novel Sesquiterpene Peroxide from Alpinia japonica (THUNB.) MIQ.
• Agarofuran-, Eudesmane-and Eremophilane-Type Sesquiterpenoids from Alpinia japonica (THUNB.) MIQ.
• 56 ハナミョウガの成分研究 : 一新セスキテルペンパーオキサイドhanalpinolの構造
• Isolation of Agarofuran-type Sesquiterpenes from Alpinia japonica (THUNB.) MIQ.
• Microbiologically Modified Chiral Synthon. III. 4,9-Dimethyl-3,5-dioxo-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids
• A Series of Sesquiterpenes with a 7α-Isopropyl Side Chain and Related Compounds Isolated from Curcuma wenyujin
• MICROBIOLOGICAL ASYMMETRIC INDUCTION OF 4,9-DIMETHYL-3,5-DIOXO-Δ^-OCTALIN
• Microbiologically Modified Chiral Synthon. II. : 4,9-Dimethyl-3,7-dioxo-Δ^-octalin for Formal Total Syntheses of Certain C(8) Oxygenated Sesquiterpenoids
• Microbiologically Modified Chiral Synthon. I. 3,8-Dioxo-4-methoxycarbonyl-9-methyl-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids and Diterpenoids
• MICROBIOLOGICALLY MODIFIED 4,9-DIMETHYL-Δ^-OCTAL-3,7-DIONES AS THE CHIRAL SYNTHON FOR FORMAL TOTAL SYNTHESES OF C(8) OXYGENATED SESQUITERPENOIDS(Communications to the Editor)
• MICROBIOLOGICAL ASYMMETRIC REDUCTION OF 4-CARBOMETHOXY-3,8-DIOXO-9-METHYL-Δ^-OCTALIN
• 60 中国産Curcuma wenyujin(温郁金)の根茎の精油から単離された数種のセスキテルペン成分の絶対構造とその生合成的関連性
• 110(P44) フェノール性オキシムの不斉酸化的閉環反応 : スピロイソオキサゾリン環を有する海洋産天然物の合成研究(ポスター発表の部)
• 29p-P-13 一次元SSDの開発 (II), データ集録系
• Studies on Tetrahydroisoquinolines. XXXVII. : A Synthesis of 3-Hydroxyaporphines and 3-Hydroxyhomoaporphines
• Biologically Active Constituents of Arnebia euchroma : Structures of New Monoterpenylbenzoquinones : Arnebinone and Arnebifuranone
• Biologically Active Constituents of Arnebia euchroma : Structure of Arnebinol, an Ansa-Type Monoterpenylbenzenoid with Inhibitory Activity on Prostaglandin Biosynthesis
• The Absolute Structure and Synthesis of Wenjine Isolated from Curcuma wenyujin
• 5. 分子の形を決める : X 線回折法を中心にして(分析技術 : こんな方法もある)
• The Diels-Alder Reaction of 3-Acetoxy-1-vinylcyclohexene with Methyl Vinyl Ketone
• THE STEREOSTRUCTURE OF WENJINE AND RELATED (1S__-, 10S__-), (4S__-, 5S__-)-GERMACRONE-1(10), 4-DIEPOXIDE ISOLATED FROM CURCUMA WENYUJIN
• THE ABSOLUTE CONFIGURATION OF REGELIDINE, A NOVEL 6-NICOTINOYL DIHYDROAGAROFURAN SESQUITERPENE ALKALOID FROM TRIPTERYGIUM REGELII(Communications to the Editor)
• ISOLATION AND STRUCTURE OF REGELIN AND REGELINOL, NEW ANTITUMOR URSENE-TYPE TRITERPENOIDS FROM TRIPTERYGIUM REGELII(Communication to the Editor)
• Revised Stereostructure for (+)-Roemecarine and Synthesis of (±)-, (+)-, and (-)-Roemercarine and (±)-Epiroemecarine
• Kinetic Resolution of (±)-4-Acyloxy-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisopuinolines by Use of Immobilized Lipases in Organic Solvents
• Studies on Tetrahydroisoquinolines. XXXII. : Conversion of 7-Hydroxy-6-methoxytetrahydroisoquinolines to 6-Hydroxy-7-methoxytetrahydroisoquinolines
• A Synthesis of Seco-mesembrane Alkaloids, (±)-Joubertiamine, (±)-Joubertinamine, and (±)-Epijoubertinamine
• Studies on Tetrahydroisoquinolines. XXXI. : A synthesis of Tetrahydroisoquinoline Dimers by Intermolecular C-O Coupling
• Synthesis of Sceletium and Amaryllidaceae Alkaloids, (±)-Mesembrine and (±)-Dihydromaritidine, (±)-Epidihydromaritidine, (±)-Elwesine, and (±)-Epielwesine(Organic,Chemical)
• Studies on Tetrahydroisoquinolines. XXVIII. : Syntheses of (±)-N-Methyllaurotetanine, (±)-Cassythicine, (±)-9-Hydroxy-1,2,3,10-tetramethoxyaporphine, (±)-Dicentrine, and (±)-Thalicsimidine
• Studies on Tetrahydroisoquinolines. XXIV. A Synthesis of Dibenzo [c, f]-1-azabicyclo [3.3.1] nonanes and Dibenzo [d, g]-1-azabicyclo [4.3.1] decanes
• Studies on Tetrahydroisoquinolines. XXII. A Stereospecific Synthesis of (±)-Srilankine and (±)-Cataline
• Studies on Tetrahydroisoquinolines. XX. A Novel Synthesis of 8-Aryl-1,2,3,4-tetrahydroisoquinolines
• Studies on Tetrahydroisoquinolines. XIX. Synthesis of (±)-Isothebaine, (±)-1-Hydroxy-2,9-dimethoxy-, (±)-1-Hydroxy-2,10-dimethoxy-, and (±)-2,10-Dimethoxy-aporphines, (±)-2,6-Dimethoxyhomomorphinandienone, and (±)-1-Hydroxy-2,10-dimethoxyhomoaporphine
• Studies on Tetrahydroisoquinolines. XVII. A Synthesis of 8-Halo-1,2,3,4-tetrahydroisoquinolines
• Regioselective Synthesis of 14-Membered Biaryl Ethers : Total Synthesis of RA-VII and Deoxybouvardin
• A Cyclization of β-Arylethylisocyanates to 3,4-Dihydroisocarbostyrils
• アポルフィンアルカロイド合成の二,三の話題
• Studies on Tetrahydroisoquinolines. VII. Synthesis of Homoaporphine via a p-Quinol Acetate ; Total Synthesis of (±)-Kreysigine
• エキソオレフィンを有するエンイン化合物の Pauson-Khand 反応とリコポジウムアルカロイド, magellanine の全合成への応用
• 86(P-20) リコポジウムアルカロイド、magellanineの合成研究(ポスター発表の部)
• 121(P-58) エキソメチレン化合物の分子内Pauson-Khand反応とリコポジウムアルカロイド、magellanine合成への応用(ポスター発表の部)
• Studies on Tetrahydroisoquinolines. XVI. Preparation of 2-Hydroxyaporphines via O-Quinol Acetates
• Organic Photochemistry. V. Dethioacetalization by Photolysis in the Presence of Molecular Oxygen
• A Novel Synthesis of Aporphine Alkaloids via o-Quinol Acetates
• Studies on Tetrahydroisoquinolines. VIII. Lead Tetraacetate Oxidation of 1,2,3,4-Tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinoline and Its 1-Substituted Derivatives
• Studies on Tetrahydroisoquinolines. XI. A Facile Synthesis of (±)-Aporphines via p-Quinol Acetates
• Studies on Tetrahydroisoquinolines. IX. The Synthesis of (±)-Domesticine and a Related (±)-Homoaporphine via p-Quinol Acetates
• ヘテロ環化学に関する本
• 研究環境を配慮した予算配分を(文部省科学研究費申請と配分の問題点)
• 有機スズ試薬を用いたカルボニル化合物のエナンチオ選択的ラジカル反応
• モンタニン型ヒガンバナ科アルカロイド, (±) -モンタニン, (±) -コクシニン, (±) -パンクラシンおよび (±) -ブルンスビジンの全合成

もっと見る 閉じる

スポンサーリンク