The Synthesis of 3-Spirooxindole Derivatives. VIII. Total Syntheses of (±)-Formosanine, (±)-Isoformosanine, (±)-Mitraphylline and (±)-Isomitraphylline

スポンサーリンク

概要

• 論文の詳細を見る

• The total synthesis of the entitled four alkaloids, which were oxindole alkaloids of Uncaria species and Mitragyna species, has been completed through several steps starting from the condensation of 2-hydroxytryptamine hydrochloride (IV) with 3,3-dimethoxy-propionaldehyde (V). The condensation product (XV) was submitted to the Michael addition with methyl vinyl ketone, followed by acid treatment to give the α, β-unsaturated ketones (XIVa, b) as two stereoisomers. The isomer (XIVb) was condensed with methyl malonate to yield the ester (XXb), which was hydrogenated with Adams' catalyst to XXIb. The compound (XXIb) was treated with dil. sulfuric acid to give the lactones (XXIIa, b) as two spiro-iso-mers, the isomer (XXIIa) of which in turn, was heated with the aminal ester, then stirred with 5% MeOH-HCl, refluxed with aq. dioxane and heated with PPA to afford (±)-for-mosanine (IIIa) and (±)-isoformosanine (IIIb). Similarly, the lactone (XXVa) which was obtained from (XXb) by reduction with NaBH_4 and hydrolysis with acid, gave (±)-mitraphylline (IIa) and (±)-isomitraphylline (IIb).

• 公益社団法人日本薬学会の論文
• 1976-04-25

著者

• 伴 義雄

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University

• 大石 武

  Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy

• 伴 義雄

  東邦大・薬

• 伴 義雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 大石 武

  北大・薬:(現)理化学研究所

• 多賀 尚正

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

• The Regioselective Dehydration of Unsymmetrical Secondary Alcohols under Mitsunobu's Reaction Conditions
• ENZYMATIC HYDROLYSIS IN ORGANIC SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE α-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES
• 29 20員環マクロライド抗生物質、ベンツリシジンの合成研究(口頭発表の部)
• 61 十字交差環化反応を用いるアルカロイド類の合成
• 23 スウィンホライドAおよびその関連化合物の合成研究(口頭発表の部)
• The Synthesis of β-Carboline Derivatives. VII. The Isolation of the Possible Intermediate in the Condensation of 3-(2-Bromoethyl) indole and 2-Halogenopyridine.
• The Synthesis of 3-Spirooxindole Derivatives. IX. The Reactions of 2-Hydroxytryptamine with Hemiacetals
• 63 Pyrrolo-1,4-benzodiazepine系抗生物質の合成
• 63 Pd触媒による一酸化炭素挿入反応を利用した1,4-Benzodiazepine骨格の合成並びにその天然物合成への応用
• 77 マイカラミドAおよび関連化合物の合成研究(ポスター発表の部)
• 72 光フリース転位反応を利用したインドールアルカロイドの合成研究
• A Facile Chemoenzymatic Route to Optically Active 4,5-Disubstituted-2E-hexenoate Derivatives. I
• Enantioselective Acetylation of an α-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents
• A Formal Total Synthesis of (-)-Oudemansin B
• A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents
• A FACILE CHEMOENZYMATIC ROUTE TO ENANTIOMERICALLY PURE 4,5-DISUBSTITUTED-2-HEXENOATE DERIVATIVES
• A LIPID LIPASE AGGREGATE AS A NEW TYPE OF IMMOBILIZED ENZYME
• Asymmetric Reduction of α-Methyl β-Keto Esters by Microbial Cells Immobilized with Prepolymer(Organic,Chemical)
• Alkylated Levoglucosan in Organic Synthesis. : A Formal Total Synthesis of Elaiophylin
• Studies on the Bischler-Napieralski Reaction with Unsaturated Lactams. Syntheses of 5,6,9,10,11,12-Hexahydro-2,3-dimethoxybenzo [4,5-a]-benzo [f] quinolizinium and Dihydrosempervirine Salts
• ELECTRONIC EFFECTS ON THE REGIOSELECTIVITY IN THE REACTIONS OF THIOALLYLIC ANIONS WITH CARBONYL COMPOUNDS
• Reduction of Nitroolefin Using Microorganisms
• Medium-Membered Ring Ketone Synsthesis. Synthesis of Oxa- and Aza-cyclooctanone Derivatives
• 64(PA2-4) 抗腫瘍活性物質エリオラニンの合成研究(ポスター発表の部)
• 44 二量体マクロリドの合成研究
• 環拡大によるラクトン環の形成とジプロジアリドおよびホラカンソリドの合成 (中・大環状天然物合成の新展開) -- (ラクトンおよびラクタムの形成反応とマクロリドおよびその関連化合物の合成)
• アシロイン縮合反応を用いた天然物の合成 (天然物化学1980B)
• 41 ステロイド水酸化阻害物質,diplodialides及び関連化合物の合成
• 生合成類似の有機合成反応--主としてインド-ルアルカロイドについて (酵素類似機能をもつ有機反応-2-)
• 59 1,2-Enediolateの反応を利用した天然物の合成研究
• 13 IBOGA ALKALOIDSの合成研究 : dl-Ibogamine,dl-Epiibogamine dl-Ibogaine,dl-Epiibogaine,dl-Tabernanthine,dl-Epitabernanthineの全合成
• A Synthesis of (±)-Dihydrodeoxyepiallocernuine by Application of a Facile Hofmann-Loeffler Type of Photocyclization
• Studies on the Structures of Some Cholestanoindoles
• The Absolute Configuration of Sarkomycin.
• Quinolizidines. VII. Structure of O-Methylpsychotrine : The Endocyclic versus the Exocyclic Double Bond Structure in the Dihydroisoquinoline Moiety
• Microbiologically Modified Chiral Synthon. III. 4,9-Dimethyl-3,5-dioxo-Δ^-octalin for Formal Total Syntheses of Certain Sesquiterpenoids
• 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
• New Synthesis of Pyrrolo-1,4-benzodiazepines by Utilizing Palladium-Catalyzed Carbonylation
• 36 Pd触媒による一酸化炭素挿入反応を用いた天然物の合成
• アリル=ジチオカルバメ-トとアルデヒドとの反応のレギオ選択性におよぼす添加物の影響 (ヘテロ原子の有機化学) -- (6族元素(硫黄,セレン,テルル))
• 37 中環状テルペン類の合成研究 : カリオフィレン類の全合成
• Chemical Synthesis of Deoxyribonucleotides Containing Deoxyadenosine at the 3'-End on a Polystyrene Polymer Support
• 18 マイトマイシン類の合成研究 : デカルバモイルオキシマイトマイシン誘導体の合成(口頭発表の部)
• 2'- AND 3'-SUBSTITUTED SANGIVAMYCINS : CONFORMATIONAL RESTRICTION BY THE GAUCHE EFFECT
• Synthesis of (+)- and (-)-cis-α-Irones
• Studies on Taxane Synthesis III.Stereocontrolled Synthesis of a Twelve-Membered Lactam Sulfide as a Precursor of 4,8,11,11-Tetramethyl-3-oxobicyclo[5.3.1]undec-8-ene
• 「基礎科学特別研究員制度」設立に関連して想う
• 高選択的新規反応の開発と有用天然物合成への応用
• Studies on Taxane Synthesis. II. : Synthese of 3,8,11,11-Tetramethyl-4-oxo- and 4,8,11,11-Tetramethyl-3-oxo-bicyclo[5.3.1]undec-8-enes Corresponding to the A- and B-Rings of Taxane Diterpenes
• Studies on Taxane Synthesis. I. : Synthesis of 3,8,11,11-Tetramethyl-4-oxobicyclo[5.3.1]undecane as a Model for Taxane Synthesis
• エリスロマイシンA合成研究をめぐって
• オリゴヌクレオチド合成技術の進歩とヒト成長ホルモン遺伝子の合成
• Meta Functionalization of Anilines and Phenol
• Medium-ring Ketone Synthesis. Synthesis of Eight- to Twelve-membered Cyclic Ketones based on the Intramolecular Cyclization of Large-membered Lactam Sulfoxides or Sulfones
• Medium-ring Ketone Synthesis. Intramolecular Acylation of Sulfur-stabilized Carbanions : A Model Study
• A NEW SYNTHETIC METHOD FOR β, γ-UNSATURATED KETONES AND A TOTAL SYNTHESIS OF EGOMAKETONE
• 大環状ラクタムスルフィドの分子内閉環反応を基盤とする中環状化合物の合成 (中・大環状天然物合成の新展開) -- (炭素環状化合物の形成反応とテルペノイドおよびその関連化合物の合成)
• Forced Nucleophilic Substitution Reaction of Chlorobenzenes bearing Electron-Donating Groups by the Use of"Naked"Methoxide Anion
• 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
• The Reactions of Activated Amides. I. The Reactions of Iminoethers derived from the Secondary Amides with the Nucleophiles
• 21 オキシインドール誘導体よりアスピドスペルマおよびイボガアルカロイドの合成に関する研究
• The Fischer Indole Synthesis with Formic Acid.I.A Convenient Synthesis of 4a-Ethyl-9-formyl-1,2,3,4,4a, 9a-hexahydro-9H-carbazole
• Asymmetric Reduction of 2-Aminobenzophenone Using Yeast, Rhodosporidium toruloides
• Activation of Weak Organic Bases. VI. The Alkylation of Thiol Esters by Triethyloxonium Salt and Diethoxycarbonium Salt (HC^^+(OC_2H_5)_2,S^^-bCl_6)
• DETERMINATION OF THE STEREOSTRUCTURE OF THE δ-LACTONES OF 5,7-DIHYDROXY-2,3-UNSATURATED ACIDS BY ^1H NMR SPECTROSCOPY(Communications to the Editor)
• Formal Total Synthesis of (-(-Indolmycin
• Fluorescence and Structure of Proteins as measured by Incorporation of Fluorophore. II. Synthesis of Maleimide Derivatives as Fluorescence-Labeled Protein-Sulfhydryl Reagents.
• Polyphosphate Esters as a Synthetic Agent. III. Amide and Peptide Syntheses
• Studies on Protein-Sulfhydryl Reagents. I. Synthesis of Benzimidazole Derivatives of Maleimide ; Fluorescent Labeling of Maleimide.
• A FORMAL SYNTHESIS OF l-α-SANTONIN FROM CHIRAL α, β-EPOXYEUDESMANOLIDE VIA ENZYME-CATALYZED HYDROLYSIS
• The Synthesis of β-Carboline Derivatives. VI. A Synthesis of 3-Ethyl-10-methoxy-12H-indolo [2,3-a] quinolizinium Salt (10-Methoxy-flavopereirine)
• A Facile Chemoenzymatic Route to Optically Active 4,5-Disubstituted-2E-hexenoate Derivatives. II
• 70 1,3-ポリオールの立体構造決定法の開発と関連天然物の合成 : ペンタマイシンの立体構造(口頭発表の部)
• P-28 酵素化学的炭素-炭素結合形成反応の開発と光学活性非糖質鍵中間体合成への応用(ポスター発表の部)
• Chemoenzymatic Carbon-Carbon Bond Formation Leading to Non-carbohydrate Derivative. Stereoselective Synthesis of Pentamycin C-11-C-16 Fragment
• Structural Characteristics of Lipid-Lipase Aggregates for Enantioselective Hydrolysis in Organic Solvents
• リパーゼを用いる光学活性ヒドロキシエステルの創製とその生理活性化合物合成への応用 : ベンツリシジンA, Bアグリコンの全合成
• The Reactions of Activated Amides. VI. The Reactions of 1-Methyl-2-pyrrolidone Dimethylacetal and 2-Methylmercapto-1-methyl-2-pyrroline with Dimethyl Acetylenedicarboxylate
• The Fischer Indole Synthesis with Formic Acid. II. The Synthesis of Hexahydrocyclopent (b) indoles
• The Synthesis of 3-Spirooxindole Derivatives. VIII. Total Syntheses of (±)-Formosanine, (±)-Isoformosanine, (±)-Mitraphylline and (±)-Isomitraphylline
• The Synthesis of 3-Spirooxindole Derivatives. VII. Total Synthesis of Alkaloids (±)-Rhynchophylline and (±)-Isorhynchophylline
• The Reactions of Activated Amides. V. The Reactions of Cyclic Amide Acetals with Electrophiles
• Activation of Weak Organic Bases. V. The Alkylation of Thiono Esters by Diethoxycarbonium Hexachloroantimonate [chemical formula], S^^-bCl_6
• Activation of Weak Organic Bases. III. The Reactions of Divalent Sulfides with Acid Chlorides in the Presence of Friedel-Crafts Catalysts
• The Reactions of Activated Amides. IV. The Reactions of Amide Acetals with Esters
• The Synthesis of 3-Spirooxindole Derivatives. IV. The Conversion of 3-Spirooxindole to Indole Derivative.
• The Synthesis of 3-Spirooxindole Derivatives. III. Stereospecific Syntheses of rac-N-Methylrhynchophyllane for Stereochemistry of Rhynchophylline and Isorhynchophylline.
• The Synthesis of 3-Spirooxindole Derivatives. II. Syntheses of 1-Methylspiro-[indoline-3,1'-pyrrolizidine and Indolizidine]-2-one.
• The Synthesis of 3-Spirooxindole Derivatives. I. Syntheses of 1-Methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3,1' (5'H)-pyrrolo [1,2-b]-isoquinoline]-2-one and its Homologs.
• β-HYDROXY-δ-LACTONES AS CHIRAL BUILDING BLOCKS INVOLVING 1,3-DIHYDROXYL FUNCTIONS. 1. : NEW STRATEGIES FOR STREOSELECTIVE CONSTRUCTION OF 2-METHYL-3,5-DIHYDROXY ESTERS
• Polyphosphate Ester as a Synthetic Agent. VII. The Beckmann Rearrangement and Formation of Amidines with PPE
• Polyphosphate Ester as a Synthetic Agent. IV. A Novel Preparation of Aryl Esters
• Polyphosphate Ester as a Synthetic Agent. V. The Fischer Indole Synthesis with Polyphosphate Ester
• Highly syn-Selective Reduction of α-Phenylthio-β-methoxy Ketones with Super-hydride
• 17 鎖状立体制御を基盤としたエリスロマイシンAの形式全合成(口頭発表の部)
• 95 ポリエンマクロライド抗生物質ペンタマイシンの合成研究(口頭発表の部)
• 有機合成化学研究室--高選択的反応と天然物合成

もっと見る 閉じる

スポンサーリンク