66 2-ピリジノン及び2-キノロン誘導体のDiels-Alder反応ダイナミシンA基本骨格合成への応用(ポスター発表の部)
スポンサーリンク
概要
- 論文の詳細を見る
Manzamine A (1) and dynemicin A (2) are potent antitumor natural products, which contain a highly substituted decahydroisoquinoline skeleton in their backbone. We have initiated our synthetic studies on these challenging molecules, focusing our attention on the search for an effective method for the construction of the required substructure. In this context, we have been interested in the Diels-Alder reaction of 3-substituted-dihydropyridinones, which was successfully applied to our synthetic approach to the manzamine A tetracyclic core. As an extention of this strategy, and in order to survey on the scope of these types of reactions, we next turned our attention to the Diels-Alder reaction of the new dienophiles, 3-phenylthio-dihydropyridin-2-ones (6) and 3-phenylthio-2-quinolones (7), in relation with the synthetic study on dynemicin A. Preparation of the requisite dienophiles are summarized in Scheme II and Scheme III. Thus, various N-protected 3-phenylthio-dihydropyridinones (6a〜6d) were prepared from 2-piperidone, while some 3-phenylthio-2-qunolinone derivatives (12, 15) were obtained from dihydrocarbostyril (10). Diels-Alder reaction of these dienophiles are summarized in Table I and Table II. Key factors for the successful conversion are 1) the selection of the electron-withdrawing N-protecting groups (N-COOMe, N-SO_2Ph), and 2) utilization of the proper Lewis acid catalyst (ZnBr_2, EtAlCl_2). In the final part of this presentation, we will discuss on the synthetic application to the dynemicin core structure utilizing this strategy. Towards this end, the Diels-Alder adduct (16) was successfully converted to the ene-diyne derivatives (25 and 26) as shown in Scheme IV. Attempts for the crucial cyclization from these precursors (25, 26) are now under active investigation along the line shown in Scheme V.
- 天然有機化合物討論会の論文
- 1993-09-10
著者
関連論文
- Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
- スフィンゴシンおよびその類縁体の構造とDNAプライマーゼに対する阻害活性との相関関係-生化学的ならびにコンピューター解析
- 37 脳機能改善薬を指向した光学活性フィゾスチグミンの新規簡易合成法の開発研究(口頭発表の部)
- 12 マンザミンAおよびその関連化合物の全合成(口頭発表の部)
- 102(P26) 光学活性イルシナールAの合成研究(ポスター発表の部)
- 54(P18) 海洋産脂質過酸化抑制インドールアルカロイドMartefragin Aの合成と活性(ポスター発表の部)
- 学術貢献賞受賞 村上泰興氏の業績
- 薬学会賞受賞 池上四郎氏の業績
- "夢"と"ロジック"と"アート"とを
- 日本薬学会功労賞受賞, 古賀直文氏の業績
- Tryptophan環状互変異性体の化学
- 日本薬学会学術賞受賞高野誠一氏の業績
- 第5回日仏医薬・精密化学シンポジウム
- 亀谷哲治教授(前会頭, 星薬科大学長)に国際複素環化学会賞授与さる
- 教養としての第2外国語を(薬学教育における第2外国語教育)
- やりくり苦心談
- 放射線障害防護薬剤に関する研究(第15報)インドール系化合物の放射線障害防護効力について
- 放射線障害防護薬剤に関する研究(第8報)システアミン関連化合物の放射線障害防護効力について
- 放射線障害防護薬剤に関する研究(第7報) : AETおよびその関連化合物の放射線障害防護効力について
- Radiation-Protective Agents. V. Synthesis and Hydrolysis of 2-(2-Aminoethylthio) indole Derivatives
- Radiation-Protective Agents. IV. Synthesis of Tetrahydro-β-carbolines and 2-Aminothiazoline Derivative from Tryptophanols
- Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. IV. Stability of N-Ethyl Derivatives of 2-Aminoethylisothiuronium Salt
- Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. II. Spectrophotometric Studies on the Reductivities of 2-Mercaptoethylamine, 2-Mercaptoethyl-, and 3-Mercaptopropyl-guanidine.
- Radiation-protective Agents. II. The Transformation of 2-(2-Aminoethyl)thiopseudoureas to 2-Amino-2-thiazolines
- Radiation-protective Agents.I. Studies on N-Alkylated-2-(2-aminoethyl)thiopseudoureas and 1,1-(Dithioethylene)diguanidines
- Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. I. Hydrogen Ion Liberation of 2-Aminoethylisothiuronium and 3-Amino-propylisothiuronium Bromide Hydrobromide
- On the Reaction of N, N'-Dimethylfumaranilide with Aluminium Chloride
- 66 2-ピリジノン及び2-キノロン誘導体のDiels-Alder反応ダイナミシンA基本骨格合成への応用(ポスター発表の部)
- The ^1H- and ^C-Nuclear Magnetic Resonance Spectra of Manzamine C and Related Compounds
- Alkylation of 3,4-Dihydro-β-carboline
- 53 海産抗腫瘍性アルカロイドマンザミン類の合成研究(口頭発表の部)
- スフィンゴ糖脂質の合成
- The Pictet-Spengler Reaction of N_b-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism
- Reactions of the Cyclic Tautomer of 3-Indoleacetamides. : Synthesis of N_b-Methyl-4,5,6-tribromo-3-indoleacetamide
- 2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-β-carbolines. : The Pictet-Spengler Reaction of N-Hydroxytryptamine with Aldehydes
- 抗ウイルス性海洋天然物ユ-ディストミンの合成
- 1-(1-Pyrrolin-2-yl)-β-carbolines. Synthesis of Eudistomins H, I, and P
- 19 抗ビールス性海洋天然物ユーデストミンの合成 : Pictet-Spengler反応の新展開(口頭発表の部)
- Synthetic Approaches to Fumitremorgins. III. : Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C
- 生体内類似反応によるトリプトファン代謝産物の合成研究
- 61 フミトレモルジンBおよび関連化合物の合成
- Inverted Prenylation of N_b-Methoxycarbonyltryptamine. Synthesis of 3a-(1,1-Dimethylallyl) pyrrolo [2,3-b] indole and 2-(1,1-Dimethylallyl) tryptamine Derivatives
- Cyclic Tautomers of Tryptophans and Tryptamines. VIII. Cyclic Tautomers of cyclo-L-Prolyl-L-tryptophyl and Related Compounds
- 28 フミトレモルジン合成へのアプローチ
- Formation and Reactions of the Cyclic Tautomers of Tryptophans and Tryptamines. VII. Hydroxylation of Tryptophans and Tryptamines
- Synthesis of the Imidazo [1,2-a] indole-spirolactone Ring System by Oxidative Double Cyclization. A Synthetic Approach to Tryptoquivalines
- Cyclic Tautomers of Tryptophans and Tryptamines. VI. Preparation of N_a-Alkyl-, 5-Chloro-, and 5-Nitrotryptophan Derivatives
- 22 Tryptoquivaline類合成へのアプローチ : Double cyclizationによる2,3,3a,4-tetrahydro-1H-imidazo[1,2-a]indole-4-Spiro-5'-γ-butyrolactoneの合成
- 22 Tryptoquivaline類合成へのアプローチ : Double cyclizationによる2,3,3a,4-tetrahydro-1H-imidazo[1,2-a]indole-4-Spiro-5'-γ-butyrolactoneの合成
- 22 Tryptoquivaline類合成へのアプローチ : Double cyclizationによる2,3,3a,4-tetrahydro-1H-imidazo[1,2-a]indole-4-Spiro-5'-γ-butyrolactoneの合成
- 22 Tryptoquivaline類合成へのアプローチ : Double cyclizationによる2,3,3a,4-tetrahydro-1H-imidazo[1,2-a]indole-4-Spiro-5'-γ-butyrolactoneの合成
- 5 ギ酸中でのTryptamine誘導体の増感酸素化反応.rac-Folicanthine,rac-Chimonanthineの合成
- Dye-sensitized Photooxygenation of Tyrptophan : 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine
- Bromination of 2-Bromo, 2-Ethylthio, and 2-Ethylsulfonylindoles with N-Bromosuccinimide. Isolation and Reactions of 1-Bromoindoles and 3-Bromoindolenines
- Reaction of Skatole with Iodine in the Presence of Thiourea
- 2-Indolinethiones. Tautomerism and Oxidation to the Disulfides
- Preparation of 3-Arylindoles
- Preparation of 3-Substituted 2-Indolinethiones via Diindolyl Disulfides. The Reaction of 3-Substituted Indoles with Sulfur Monochloride
- オクテット
- Halogenation of 1-Substituted Skatoles. Preparation of 3-Bromomethylindoles
- 94(P12) 有機金属反応を利用した簡易ケトン合成とダイネミシンAモデル合成への応用(ポスター発表の部)
- P-31 光学活性イルシナール類合成へのアプローチ(ポスター発表の部)
- 有機化学者のための蛋白質過剰生産
- Reaction of Tryptamine and Aniline with δ-Valerolactone and Its Dehydro Derivatives. A New Synthesis of 1,2,3,4,6,7,12,12b-Octahydroindolo [2,3-α] quinolizine
- Bromination of 3-tert-Butylindoles with N-Bromosuccinimide
- 有機化学者のための蛋白質過剰生産
- 抗ウイルス性海洋天然物ユーディストミンの合成
- Pyranoindole and Thiopyranoindole. Oxidative Cyclization of 3-Indolepropanol and 3-Indolepropanethiol with N-Bromosuccinimide, N-Chlorosuccinimide, and Singlet Oxygen
- SYNTHESIS OF (±)-FLUSTRAMINE B, A MARINE ALKALOID
- The Fragmentation of Some Oxindoles and 2-Indolinethiones induced by Electron Impact
- Thiation of Oxindoles
- The Acetylation of 3-Acylindoles
- Indole誘導体の光増感酸素化反応--Tryptophanおよび関連化合物を中心として (天然物化学′80A)
- インド-ル環の反応性--3位側鎖の関与する反応を中心として (現代の生命化学--トリプトファンをめぐって)
- インドール誘導体と酸素分子との反応 : 合成化学と生命化学への貢献を心掛けて
- インドール系化合物の光増感酸素化反応について
- 2-インドリンチオンの化学
- Bromination of Skatole. A Simple Preparation of 3-Methyloxindole and 2-Bromo-3-methylindole.