Practical Syntheses of [R]- and [S]-1-Alkylamino-3-aryloxy-2-porpanols from a Single Carbohydrate Precursor

スポンサーリンク

概要

• 論文の詳細を見る

• A practical synthetic route to optically active [2R]- and [2S]-1-alkylamino-3-aryloxy-2-propanols (β-blockers) from [2R]-2,3-O-isopropylideneglyceraldehyde ([R]-1) was developed. Synthesis of the [S]-isomers was carried out as follows. Borohydride reduction of [R]-1 in the presence of excess alkylamine followed by alkoxycarbonylation, acid hydrolysis, and cyclization under K_2CO_3 catalysis gave [5S]-3-alkyl-5-hydroxymethyl-1,3-oxazolidin-2-ones, the tosylates of which were coupled with various phenols then hydrolyzed by alkali treatment to give [S]-(-)-β-blockers (e. g., propranolol, carteolol) in satisfactory yields. [R]-, [S]-, and rac-pindolol were synthesized from the corresponding 3-isopropyl-5-(2-methyl-3-nitrophenoxymethyl)-1,3-oxazolidin-2-one by application of the Leimgruber-Batcho method.

• 公益社団法人日本薬学会の論文
• 1981-12-25

著者

• 津田 喜典

  金沢大学

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉本 公浩

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 吉本 公浩

  金沢大学薬学部

• 西川 照美

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 西川 照美

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

• 糖類水酸基の一選択的修飾と変換 : スズ化合物による水酸基の選択的活性化
• Studies on Crude Drugs Effective on Visceral Larva Migrans. IV. : Isolation and Identification of Larvicidal Principles in Pepper
• Studies on Crude Drugs Effective on Visceral Larva Migrans. III. : The Bursting Activity of Tannins on Dog Roundworm Larva
• Studies on Crude Drugs Effective on Visceral Larva Migrans. II. : Larvicidal Principles in Kaempferiae Rhizoma
• Studies on Crude Drugs Effective on Visceral Larva Migrans. I. Identification of Larvicidal Principles in Betel Nuts(Pharmacognosy,Chemical)
• A Convenient Synthesis of Tertiary Amines by Alkylation of Secondary Amines with Alkyl Halides in the Presence of Potassium Hydride and Triethylamine
• Stereoselective Introduction of Oxygen Functionalities at the 11β-Position of Erythrinan Skeleton : Total Syntheses of (±)-Erythristemine and (+)-Erythrartine
• Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (5). Cyclization of Perhydro-2-epoxymethylene-6-oxo-6H-pyrido[2,1-i]indole-1-acetic Acid : Synthesis of 8-Oxoerythroidans
• Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids.(3). Synthesis of β-Erythroidine Skeleton (β-Erythroidan)
• Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic δ-Lactones
• Anthelmintic Effect of the Embelia ribes Decoction and Embelin Derivatives on Trichuris muris in Mice
• Trichuris muris : The Anthelmintic Effect of Mebendazole in Mice is Dependent upon the Pre-treatment with Steroids
• Mobility Inhibition and Nematocidal Activity of Asarone and Related Phenylpropanoids on Second-Stage Larvae of Toxocara canis
• A Tetrazorium Dye (MTT) Assay for Testing Larval Viability Using Second-Stage Larvae of Toxocara canis
• Nematocidal Activity of Turmeric : Synergistic Action of Curcuminoids
• Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae
• Nematocidal Principles in "Oakmoss Absolute" and Nematocidal Activity of 2,4-Dihydroxybenzoates
• Studies on Crude Drugs Effective on Visceral Larva Migrans. V. : The Larvicidal Principle in Mace (Aril of Myristica fragrans)
• Chiral Synthesis of Erythrina Alkaloids. (2). Synthesis of enantio-Type Erythrinan Alkaloids Utilizing Asymmetric Acylation and Kinetic Resolution of Diastereomers
• CHIRAL SYNTHESIS OF ENANTIO-TYPE ERYTHRINAN ALKALOIDS UTILIZING ASYMMETRIC ACYLATION AND KINETIC RESOLUTION OF DIASTEREOMERS
• 4,4-Dimethyl Effect. (7). The A-Ring Conformation of 4,4-Dimethyl-3-keto Steroids in Solution. The Circular Dichroism Spectra of Onoceranediones
• 4,4-Dimethyl Effect (2). Syntheses, ^1H- and ^C-Nuclear Magnetic Resonance Spectra, and the Conformations of 6α- and 6β-Substituted-1,1,10β-trimethyl-trans-decal-2-ones (8α- and 8β-Substituted-4,4,10β-trimethyl-trans-decal-3-ones), Models of 4,4-Dimet
• Barbaloin Stimulates Growth of Eubacterium sp. Strain BAR, a Barbaloin-Metabolizing Bacterium from Human Feces
• 4,4-Dimethyl Effect. (3). The Ring A Conformation of 4,4-Dimethyl-Δ^7-3-keto Steroids and 4,4,8-β-Trimethyl-3-keto Steroids (3-Keto-triterpenoids). The Crystal Structure of Serratenedione
• SYNTHESES OF THE β-ERYTHROIDINE SKELETON(Communications to the Editor)
• 90(P04) β-エリスロイジンの合成研究(ポスター発表の部)
• ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
• A Stable Monosubstituted Isoindole Derivative : The Crystal Structure of 1-(1,2,3-1H-Benzotriazol-1-yl)-2-(4-methylphenyl)-2H-isoindole
• REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
• Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
• Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
• Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
• Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions
• Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
• Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
• 茯苓の研究-1-菌核の産出状況および形態
• 色彩計による生薬の品質評価-1-粉末生薬の測定条件と人参類生薬の品質評価
• Reaction of Phenylselenenyl Chloride with Δ^2-Erythrinans in Methanol : Conformational Fluctuation and Stereochemical Pathway
• Hydride Reduction of Erythrinan-7,8-diones and 7-O-Methanesulfonyl-8-oxo-erythrinans
• Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
• Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
• Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
• Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
• Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene : Stereochemistry of the Cycloadducts
• Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
• Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (4). Oxidation of Furan Ring of D-Furanoerythrinans with N-Bromoacetamide
• Regioselective Syntheses of Mono-O-acylglucoses
• SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
• Regioselective Monotosylation of Non-protected and Partially Protected Glycosides by the Dibutyltin Oxide Method
• 4,4-Dimethyl Effect. (4). The Conformation of α-Onoceradienedione in the Crystalline State
• Regioselective Introduction of a Methoxy Group at the Benzylic Position of Isochromane Derivatives by Cerium(IV) Oxidation in Methanol
• SYNTHESIS OF COCCULOLIDINE SKELETON, A NON-AROMATIC NOR-ERYTHRINAN ALKALOID(Communications to the Editor)
• REGIOSELECTIVE INTRODUCTION OF p-COUMAROYL GROUP TO α-L-ARABINO-PYRANOSIDES. TOTAL SYNTHESES OF INUNDOSIDE-G AND INUNDOSIDE-D_1
• Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates
• 26 ホモエリスリナアルカロイド,(±)schelhammericine,(±)3-epischelhammericineの全合成
• TOTAL SYNTHESIS OF THE HOMOERYTHRINAN ALKALOIDS, SCHELHAMMERICINE AND 3-EPISCHELHAMMERICINE
• Conversion of Thiocarbonyl into Carbonyl Group by O-S Exchange Reaction with Dibutyltin Oxide or Bistributyltin Oxide
• Total Synthesis of Hydroxyhopanone
• Synthesis of Malabaricones, Diarylnonanoids Occurring in Myristicaceous Plants
• A NEW 1,2-CARBONYL TRANSPOSITION METHOD VIA PHENYLSELENENYLATION. HIGH YIELD TRANSFORMATION OF O-METHYLESTRONE TO O-METHYLISOESTRONE
• Infrared Spectra of Conjugated Amides : Reassignment of the C=O and C=C Absorptions
• Synthesis and Nematocidal Activity of Hydroxystilbenes
• 68 二,三の天然アシル化糖およびアシル化配糖体の合成 : 糖類に対する位置選択的アシル基の導入
• スピロ型構造を持ったアルカロイド群の全合成
• 日本薬学会奨励賞受賞森裕二氏の業績
• 白樺6大学合同セミナーなど(研究者の能力を高めるために実行している教育)
• ヒガンバナ科アルカロイドの全合成
• "薬とは何か"の化学(薬品化学で何を教えるか)
• 日本薬学会学術賞紹介-2 : 藤田栄一氏の業績
• 医薬品の開発と天然物化学(薬学領域において天然物化学研究に託される役割り)
• I-C-9 腸内細菌による和漢薬成分の代謝(第 22 報) : Eubacterium sp. BAR における Barbaloin 代謝酵素の誘導
• New Method for Isomerization of (Z)-Stilbenes into the (E)-Isomers Catalyzed by Diaryl Disulfide
• CHEMISTRY OF OXO-SUGARS (1). REARRANGEMENT OF 2-OXOGLYCOSIDES IN PYRIDINE : EVIDENCE OF INTRAMOLECULAR HYDRIDE SHIFT
• Isolation and Structure Elucidation of Gymnemic Acids, Antisweet Principles of Gymnema sylvestre
• TRIALKYLTIN RADICAL USED TO CATALYZE THE O,S-REARRANGEMENT OF CYCLIC THIONOCARBONATES. A NEW ENTRY TO THIO-SUGARS(Communication to the Editor)
• 天然由来殺寄生虫物質
• Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates : Formation of Branched Furanosides
• TWO NEW GYMNEMIC ACID CONGENERS CONTAINING A HEXULOPYRANOSIDE MOIETY
• Z-E Isomerization of β-Methoxychalcones : Preferred Existence of E-Isomers in Naturally Occurring β-Methoxychalcones
• Regio- and Stereo-Selective Transformation of Glycosides to Amino-glycosides : Practical Synthesis of Amino-sugars, 4-Amino-4-deoxy-D-galactose, 4-Amino-4-deoxy-L-arabinose, 3-Amino-3-deoxy-D-allose, 3-Amino-3-deoxy-D-glucose, 3-Amino-3-deoxy-D-ribose, 3-
• Regioselective Mono-oxidation of Non-protected Carbohydrates by Brominolysis of the Tin Intermediates
• Selective Deoxygenation via Regioselective Thioacylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method(Organic,Chemical)
• Hexahydro-dibenz[d, f]azecines : Existence of Two Conformational Isomers of the 6-Oxo Derivatives in Solution
• Regioselective Monoalkylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method
• The Alkaloidal Constituents of Goda-Manel (Crinum zeylanicum L.), a Sri Lankan Folk Medicine
• A Highly Stereoselective Synthesis of rel[1R, 3R, 7R, 9S]9-Acetoxy-8,8-dimethyltricyclo[5.4.0.0^]undecan-4-one, a Versatile Intermediate to Terpenoids. Synthesis of α-Onocerin
• ^C-Nuclear Magnetic Resonance (NMR) Spectra of O-Acylglucoses. Additivity of Shift Parameters and Its Application to Structure Elucidations
• Syntheses and ^1H- and ^C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Methyl Mono-O-tetradecanoyl-a- and β-D-Glucopyranosides
• REGIOSELECTIVE MONO-OXIDATION OF NON-PROTECTED GLYCOSIDES BY THE BIS-TRIBUTYLTIN OXIDE-BROMINE METHOD
• 4,4-Dimethyl Effect. (6). The Ring A Conformation of 4,4-Dimethyl-3-keto Steroids and Triterpenoid-3-ketones : Predicted and Observed Geometries and Their Chiroptical Properties
• 4,4-Dimethyl Effect. (5). The Conformation of 8αH, 14βH-Onocerane-3,21-dione (Onoceranedione-I) in the Crystalline State
• アシル化糖の位置選択的合成とその転位 : 糖類水酸基の位置選択的修飾
• On the Possibility of Direct O-1β→ -6 Acyl Migration in 1-O-Acyl-β-D-glucose Derivatives
• General Path of O-Acyl Migration in D-Glucose Derivatives : Acyl Migration of Methyl Mono-O-myristoyl-α- and β-D-Glucopyranosides and Mono-O-myristoyl-D-glucopyranoses
• REGIOSELECTIVE OXIDATION OF A β-L-ARABINOPYRANOSIDE VIA CYCLIC TIN INTERMEDIATE. FACILE SYNTHESIS OF 4-AMINO-4-DEOXY-L-ARABINOSE, AN AMINO-SUGAR FOUND IN LIPOPOLYSACCHARIDES OF SOME SALMONELLA R MUTANT STRAINS
• Practical Syntheses of [R]- and [S]-1-Alkylamino-3-aryloxy-2-porpanols from a Single Carbohydrate Precursor
• Highly Stereoselective Grignard Reaction of an Aldopyranose : A Simple synthesis of 6-Deoxy-D-idose from D-Xylose
• 色彩計による生薬の品質評価(第2報) : 大黄の色彩と含有成分量
• ネパール産カギカズラ属植物Uncaria scandensの形態とアルカロイド成分
• 色彩計による生薬の品質評価(第1報) : 粉末生薬の測定条件と人参類生薬の品質評価

もっと見る 閉じる

スポンサーリンク