Chemical Transformation of Protoberberines. XVI. Regioselective Introduction of an Oxy Functionality at the C_<12>-Position of the Benzo[c]phenanthridine Skeleton : A Convenient Synthesis of Macarpine from Oxychelirubine

スポンサーリンク

概要

• 論文の詳細を見る

• A novel method for the introduction of an oxy functionality at the C_<12>-position of the benzo[c]phenanthridine skeleton was developed. The method was successfully applied to a biomimetic synthesis of macarpine (3) from oxychelirubine (15), which was easily derived from the corresponding protoberberine (9).

• 社団法人日本薬学会の論文
• 1990-12-25

著者

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 向 智里

  金沢大学薬学部

• 向 智里

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 吉田 修治

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 趙 元済

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 笛木 司

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 向 智里

  Faculty Of Pharmaceutical Sciences Osaka University

• 趙 元済

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉田 修治

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 笛木 司

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Institute Of Natural Medicine University Of Toyama

関連論文

• Studies on Antispasmodics. VI. Synthesis of N-Alkyl 6- and 7-Diarylmethyleneindolizidinium Bromides
• Studies on Antispasmodics. V. Synthesis and Anticholinergic Activity of N-Alkyl 1- and 2-Diarylmethylene-indolizidinium Bromides
• 鎮痙剤の研究(第4報)Diarylhydroxymethylquinolizidine Methohalidesの合成と抗アセチルコリン作用
• 鎮痙剤の研究(第3報)2位置換Quinolizidine類の簡便な新合成法とそれらの立体構造について
• 鎮痙剤の研究(第2報)3位置換Quinolizidine類の簡便な新合成法とそれらの立体構造について
• Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine
• 4 Securinine及びVirosecurinineの全合成
• Total Synthesis of Securinine
• Synthesis of (±)-Methyldecamine
• Dacarbazineの光分解によって生成する発痛物質の探索
• Convenient Synthesis of 2,3,9,10-Tetraoxygenated Protoberberine Alkaloids and Their 13-Methyl Alkaloids
• 12-3-B3 ダカルバジン注射剤投与時における血管痛原因物質の探索
• 100(P24) 抗腫瘍性スチリルラクトン化合物の高立体選択的合成(ポスター発表の部)
• (o-トリメチルシリルベンズアルデヒド)クロム錯体を活用する高立体選択的反応の開発
• Erythro-Selective Aldol Reaction of Tricarbonyl(η^6-o-trialkylsilylbenzaldehyde)chromium(0) Complexes with Cyclic Ketene Silyl Acetals
• 18 Protoberberineアルカロイドの新規合成とBenzo[c]phenanthridineアルカロイド(±)-Ambinineの全合成(口頭発表の部)
• Chemical Transformation of Protoberberines. XVII. Biomimetic Introduction of an Oxy Functionality at the C-10 Position in the Benzo[c]phenanthridine Skeleton : Synthesis of 2,3,7,8,10-Pentaoxygenated Benzo[c]phenanthridine Alkaloids, Chelilutine and Sangu
• A FIRST TOTAL SYNTHESIS OF (±)-AMBININE
• Chemical Transformation of Protoberberines. XVI. Regioselective Introduction of an Oxy Functionality at the C_-Position of the Benzo[c]phenanthridine Skeleton : A Convenient Synthesis of Macarpine from Oxychelirubine
• Trimethylsilyl Trifluoromethanesulfonate-Catalyzed Aldol Reaction of Various Aldehydes with Silyl Enol Ethers
• A NOVEL DIASTEREOSELECTIVITY IN THE ALDOL REACTION OF CYCLIC KETENE SILYL ACETALS WITH COBALT-COMPLEXED AND UNCOMPLEXED PROPYNALS
• 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
• SYNTHESIS OF 3-SUBSTITUTED ISOCOUMARINS THROUGH ACYLOXYPALLADATION OF o-ALKENYLBENZOIC ACIDS
• A NOVEL SYNTHESIS OF QUINAZOLINEQUINONE AND CARBAZOLEQUINONE THROUGH ANIONIC CYCLOADDITION : ITS APPLICATION TO A SYNTHESIS OF MURRAYAQUINONE A
• Re-examination of the Synthesis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinylphenyl)iso carbostyril
• Synthesis of Pyrido[4,3-d]pyrimidin-5(6H)-ones via Anionic Cycloaddition of Methyl 2,4-Dimethoxy-6-methyl-5-pyrimidinecarboxylate with Imines
• Synthetic Studies on Anthracyclinones. XIII. Conversion of Bisanhydro-γ-rhodomycinone into Bisanhydrodaunomycinone
• 2-Oxo-1,2,3-oxathiazolidines. Its Application to Separation of Diastereoisomers of β-Amino-alcohols, 6-(4-Methoxy-2-piperidyl)-1,4-dioxaspiro [4,5] decan-6-ol and 2-Hydroxy-2-(2-piperidyl) cyclohexanone
• Synthetic Studies on Securitinine and Related Compounds. II. A Synthesis of 10a-Episecuritinine
• Synthetic Studies on Securitinine and Related Compounds. I. Stereochemistries of the Catalytic Hydrogenation Products of 6-(4-Methoxy-2-pyridyl)-1,4-dioxaspiro [4,5] decan-6-ol
• 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
• ウラジロガシ(Quercus stenophylla MAKINO)の成分研究 : 第1報 ウラジロガン葉よりFriedelinの分離
• Intramolecular Cyclization of 6-Hydroxy-6-(2-piperidyl)-2-cyclohexene-Δ^-acetic Acid γ-Lactone, a Degradation Product of Securinine
• Synthesis of Racemic Loliolide
• Structure of Securitinine.
• Convenient Synthesis of 6-(1-Acetyl-2-piperidyl)-6-hydroxy-2-cyclohexene-Δ^-acetic Acid γ-Lactone, the Key Intermediate in Total Synthesis of Securinine
• Structure of Securitinine
• Hofmann Degradations of Tetrahydrosecurinine and Tetrahydrosecurininol. Stereochemistry at C-3a of Tetrahydrosecurinine
• Synthesis and Stereochemistry in B/C Ring Juncture of Lactamcarbinol A, a Degradation Product of Securinine
• 学術貢献賞受賞 北 泰行氏の業績
• 故荒田義雄先生を偲んで
• イソキノリンアルカロイドの生合成的合成
• サマリーを重要視(キーワードの使い方)
• 科学研究費の配分について(文部省科学研究費申請と配分の問題点)
• 双環状アミン体から中環状アミン類の合成
• Synthetic Studies on Lythraceae Alkaloids. V. Total Synthesis of (±)-Vertaline
• Synthetic Studies on Lythraceae Alkaloids. IV. Total Synthesis of (±)-Methyldecinine
• Total Synthesis of (±)-Lagerine
• Synthetic Studies on Lythraceae Alkaloids. III. Stereoselective Total Synthesis of (±)-Decaline
• Synthetic Studies on Lythraceae Alkaloids. II. The Mannich Reaction of Isopelletierine with 3-Methoxybenzaldehyde and 3-Hydroxybenzaldehyde
• Studies on 1-Azabicyclo Compounds. XXIV. Synthesis and Stereochemistry of 10-Ethyl-, 10-Vinyl-, and 10-Ethynyl-quinolizidine Methiodides
• Studies on 1-Azabicyclo Compounds. XXII. Stereochemistry of 9a-Substituted Quinolizidine Methiodides
• Chemical Transformation of Protoberberines. XV. : A Novel and Efficient Method for the Introduction of Alkyl Groups on the C-13 Position in the Protoberberine Skeleton
• A NOVEL TOTAL SYNTHESIS OF (±)-CRYPTAUSTOLINE, A DIBENZOPYRROCOLINE ALKALOID
• A NOVEL AND BIOMIMETIC SYNTHESIS OF CHELILUTINE AND SANGUILUTINE
• A TOTAL SYNTHESIS OF (±)-CEPHALOTAXINAMIDE
• 64 ProtoberberineアルカロイドからBenzo [c] phenanthridineアルカロイドの生合成的合成(口頭発表の部)
• 58 ProtoberberineアルカロイドからBenzo[c]phenanthridineアルカロイドの高立体選択的合成
• 33 ProtoberberineからBenzo〔c〕phenanthridine及び3-Arylisoquinolineアルカロイドの合成
• Chemical Transformation of Protoberberines. VIII. A Novel Synthesis of (±)-Fumaricine and a Formal Synthesis of (±)-Alpinigenine
• Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8,14-Cycloberbines
• Chemical Transformation of Protoberberines. V. Photochemical Valence Isomerization of Berberinephenolbetaines to 8,14-Cycloberbines, Versatile Aziridine Derivatives for a Novel and Efficient Entry to Spirobenzylisoquinolines and Benzindenoazepines
• Transformation of (±)-Ophiocarpine and (±)-13-Epiophiocarpine to (±)-α- and (±)-β-Hydrastine with Complete Retention of Configuration
• Chemical Transformation of Protoberberines. XIII. A Novel and Efficient Synthesis of Antitumor Benzo[c]phenanthridine Alkaloids, Nitidine and Fagaronine(Organic,Chemical)
• Chemical Transformation of Protoberberines. XI. A Novel Synthesis of 2,3,10,11-Tetraoxygenated Protoberberine Alkaloids from Corresponding 2,3,9,10-Tetraoxygenated Protoberberine Alkaloids(Organic,Chemical)
• SYNTHESIS OF FAGARIDINE, A PHENOLIC BENZO [c] PHENANTHRIDINE ALKALOID
• Two New Triterpenes from the Rhizome of Dryopteris crassirhizoma, and Inhibitory Activities of Its Constituents on Human Immunodeficiency Virus-1 Protease
• Enantioselective Dehydroxylation of Enterodiol and Enterolactone Precursors by Human Intestinal Bacteria(Pharmacognosy)
• Developing of anti-HIV agents from natural resources(Chemical & Pharmacological study)
• A New Enzyme Immunoassay for Aconitine and Its Application to Quantitative Determination of Aconitine Levels in Plasma(Pharmacognosy)
• Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase
• Flavanone and Flavonol Glycosides from the Leaves of Thevetia peruviana and Their HIV-1 Reverse Transcriptase and HIV-1 Integrase Inhibitory Activities
• Inhibition of Cytopathic Effect of Human Immunodeficiency Virus Type-1 by Various Phorbol Derivatives
• Inhibitory effects of flavonoids on human immunodeficiency virus type-I integrase
• The Heterocyclic Ring Fission and Dehydroxylation of Catechins and Related Compounds by Eubacterium sp.Strain SDG-2, a Human Intestinal Bacterium
• Triterpenes from the Spores of Ganoderma lucidum and Their Cytotoxicity against Meth-A and LLC Tumor Cells
• Inhibition of Human Immunodeficiency Virus Type 1 Reverse Transcriptase and Ribonuclease H Activites by Constituents of Juglans mandshurica
• Inhibitory Effects of Constituents from Cynomorium songaricum and Related Triterpene Derivatives on HIV-1 Protease
• Triterpenes from the Spores of Ganoderma lucidum and Their Inhibitory Activity against HIV-1 Protease
• Isolation and Characterization of a Human Intestinal Bacterium, Eubacterium sp. ARC-2, Capable of Demethylating Arctigenin, in the Essential Metabolic Process to Enterolactone(Pharmacology)
• Inhibitory effect of Yunnan traditional medicines on hepatitis C viral polymerase
• Isolation of a Human Intestinal Bacterium That Transforms Mangiferin to Norathyriol and Inducibility of the Enzyme That Cleaves a C-Glucosyl Bond(Pharmacognosy)
• An Improved Synthesis of Butyl 4-[(4-Amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)
• Synthesis and Gastrointestinal Prokinetic Activity of Novel Benzamide Derivatives with Amphoteric Side Chains
• New Triterpenoid Saponins from the Roots of Sinocrassula asclepiadea
• INVERSION OF A HYDROXYL GROUP BY THE NEIGHBORING-GROUP PARTICIPATION OF A URETHANE : A GENERAL AND STEREOSELECTIVE SYNTHESIS OF (±)-RADDEANONE, (±)-YENHUSOMIDINE, AND RELATED SPIROBENZYLISOQUINOLINE ALKALOIDS
• A CONVENIENT TRANSFORMATION OF SPIROBENZYLISOQUINOLINES TO DEHYDROPHTHALIDEISOQUINOLINES
• Chemical Transformation of Protoberberines. XII. : A Novel Synthesis of Rhoeadine Alkaloids. : An Alternative Synthesis of a Key Intermediate, Benzindenoazepine, for a Synthesis of (±)-cis-Alpinigenine and (±)-cis-Alpinine from Palmatine(Organic,Chemical)
• A FIRST AND STEREOSELECTIVE SYNTHESIS OF (±)-RADDEANAMINE
• A NOVEL AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (±)-SIBIRICINE
• Chemical Transformation of Protoberberines. VI. Ring D Inversion of Protoberberine Alkaloids. Conversion of Berberine into Non-naturally Occurring 11,12-Oxygenated Protoberberines via Spirobenzylisoquinolines
• 54 8,14-Cycloberbineを経由するProtoberberineアルカロイドからSpirobenzylisoquinoline及びBenzindenoazepineアルカロイドの合成
• 26 Lythraceaeアルカロイドの合成 : (±)-Decaline,(±)-Vertaline,(±)-Desmethyldecaline,(±)-Methyldecinine,(±)-Methyllagerineの全合成

もっと見る 閉じる

スポンサーリンク