Amino Acids and Peptides. III. A New Synthetic Approach to N-Acylated α-Amino Aldehydes from N-Acylated α-Amino Acids by Catalytic Reduction of Their Mixed Carbonic-Carboxylic Acid Anhydrides with Palladium-Charcoal

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概要

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• Mixed carbonic-carboxylic acid anhydrides prepared from N-acylated α-amino acids and ethyl chloroformate in tetrahydrofuran were reduced to the corresponding N-acylated α-amino aldehydes with palladium-charcoal under hydrogen bubbling. The optimum conditions found for N-acetyl-L-alanine were applied to the conversion of several kinds of N-acylated α-amino acids to their corresponding aldehydes, as shown in Table II. It was found that considerable racemization occurred under the present reduction conditions. Oxidation of some N-acylated β-amino alcohols with dimethylsulfoxide in the presence of dicyclohexylcarbodiimide and phosphoric acid was also studied.

• 公益社団法人日本薬学会の論文
• 1972-02-25

著者

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 関 秀雄

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)fujisawa Pharmaceutical Co.

関連論文

• Amino Acids and Peptides. XXIII. An Asymmetric Synthesis of (R)-(-)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine
• Stereochemical Studies. XIII. Determination of the Absolute Configuration of Mercaptosuccinic Acid by Chemical Correlation with Glyceraldehyde
• Chemistry of Amino Acids. IV. Decarboxylation of 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid and Its Derivatives
• Studies on Opically Active Amino Acids. VII. Stereoselective Synthesis of l-Norephedrine Hydrochloride from D-Phenylalanine
• Studies on Optically Active Amino Acids. V. Synthesis of Optically Active α-Aminoalcohols by the Reduction of α-Amino Acid Esters with Sodium Borohydride
• Studies on Optically Active Amino Acids. IV. A New Synthetic Approach to Chloramphenicol Base from L-Phenylalanine.
• Studies on Thioamides. I. Synthesis of N-(2-Arylethyl)-thioamides and their Infrared Absorption Spectra.
• The Reductive Cyclization of 1-Methyl-3-aminoalkyloxindoles with Lithium aluminum Hydride.
• Stereochemical Studies. XXXVIII. Asymmetric Synthesis of the Key Compounds for the Synthesis of optically Active Diterpenes. Asymmetric Synthesis of optically Active 1,2,3,4,5,6,7,8,8a-Octahydro-8a-methyl-3,8-naphthalenedione Derivatives with L-Proline De
• 立体化学の研究(第33報)L-Proline誘導体を用いたEnamineの不斉誘起反応による不斉合成(-)-Bisdehydroestrone Methyl Etherの不斉合成
• 立体化学の研究(第32報)L-Proline誘導体を用いたEnamineの不斉誘起反応による不斉合成, ステロイドならびにテルペン合成中間体の不斉合成
• Stereochemical Studies. XXIX. Asymmetric Synthesis of 2-Alkylcyclohexanones via optically Active Lithioenamines
• Stereochemical Studies. XXVIII. Some Aspects of the Asymmetric Synthesis of (R)-(+)-4-Methyl-4-phenyl-2-cyclohexenone via an Enamine
• Stereochemical Studies.XX.Asymmetric Synthesis of α-Bromoketones
• Stereochemical Studies.XIX. Asymmetric Synthesis of 2-Alkyl-4-substituted Cyclohexanones with Enamine Alkylation
• Stereochemical Studies. IX. Asymmetric Synthesis of 2-Alkylcyclo-hexanones with Enamine Alkylation
• Chemistry of Amino Acids. V. Studies on α-Alkyl-α-amino Acids. IX. Mild Hydrolytic Ring Cleavage of Hydantoin Derivatives
• Studies on Optical Rotatory Dispersion and Circular Dichroism. II. Circular Dichroism of α-Hydroxy-and α-Amino-α-phenyl Ketones
• Stereochemical Studies. VII. Thermal Rearrangement of α-Hydroxyimines to α-Aminoketones using optically Active Open Chain Compounds
• Studies on optically Active Amino Acids. XVIII. Studies on α-Methyl-α-amino Acids. XIV. Several Optical Properties of α-Methyl-α-amino Acids
• Studies on Optically Active Amino Acids. XIV. Studies on α-Alkyl-α-amino acids. VII. Determination of Absolute Configuration of Optically Active α-Methylphenylglycine Configuration of Optically Active α-Methylphenylglycine and 1-Methyl-1-phenylpropylamine
• Stereoselective Reactions. XVI. : Total Synthesis of (-)-β-Bourbonene by Employing Asymmetric (2+2) Photocycloaddition Reaction of Chiral Butenolide
• Pyrimidine Derivatives. V. Structure-Activity Studies of Antihypertensive Quinazoline Derivatives Using the Adaptive Least-Squares Method
• Pyrimidine Derivatives. VII. Structure-Activity Relationship of Hypoglycemic 4-Amino-2-(1-piperazinyl) pyrimidines investigated by the Adaptive Least-Squares Method
• Pyrimidine Derivatives. VI. Synthesis of 2-(1-Piperazinyl)-5,6-polymethylenepyrimidine Derivatives and Determination of Their Hypoglycemic Activity
• Stereochemical Studies. LIX. Asymmetric Transamination from (S)-α-Amino Acids. Synthesis of optically Active Amines by Chemical Transamination of (S)-α-Amino Acid Esters to Ketones
• SYNTHESIS OF L-TRYPTOPHAN FROM L-GLUTAMIC ACID
• Pyrimidine Derivatives. II. New Synthesis and Reactions of 4-Amino-2-methylthiopyrimidine Derivatives
• Amino Acids and Peptides. XXX. Phosphorus in Organic Synthesis. XVII. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to Solid-phase Peptide Synthesis
• Stereoselective Reactions. II. Asymmetric Synthesis of β-Substituted Aldehydes by Michael Reaction using Chiral α, β-Unsaturated Aldimines
• Stereoselective Reactions. I. A highly Efficient Asymmetric Synthesis of β-Substituted Aldehydes via 1,4-Addition of Grignard Reagents to optically Active α, β-Unsaturated Aldimines
• Stereochemical Studies. LIV. A Biogenetic-type Asymmetric Synthesis of optically Active Galanthamine from L-Tyrosine
• Stereochemical Studies. LIII. An Asymmetric Synthesis of (3S 15S 20R)-Yohimbone from L-Tryptophan by 1,3-Transfer of Asymmetry
• Synthesis of Formamidines from Carbodiimides with Sodium Borohydride in Isopropanol
• Amino Acids and Peptides. XXIX. A New Efficient Asymmetric Synthesis of α-Amino Acid Derivatives with Recycle of a Chiral Reagent-Asymmetric Alkylation of a Chiral Schiff Base from Glycine
• MOLECULAR RECOGNITION AND DISCRIMINATION OF HYDROPHOBIC GUESTS IN WATER BY QUATERNARY AMMONIUM CYCLOPHANES HAVING DIARHLMETHANE UNITS
• DESIGN, SYNTHESIS, AND PROPERTIES OF NOVEL WATER-SOLUBLE CYCLOPHANES HAVING NAPHTHYLPHENYLMETHANE UNITS AS HOSTS FOR ALIPHATIC AND AROMATIC GUESTS
• ASYMMETRIC REDUCTION OF ARYLGLYOXYLIC ACIDS VIA・HOST-GUEST COMPLEX FORMATION WITH OPTICALLY ACTIVE PARACYCLOPHANES
• Stereochemical Studies. XXIII. Stereochemistry of the Thermal Isocyanide-Cyanide Rearrangement
• Stereochemical Studies. XLVII. Asymmetric Reduction of 2-Alkyl-1,3,4-cyclopentanetriones with Lithium Aluminum Hydride decomposed by optically Active β-Aminoalcohols. Syntheses of optically Active Allethrolone and Prostaglandin E_1
• Stereochemical Studies. XLV. A Novel Regiospecific Ring Opening of optically Active 2-Substituted-1-tosylaziridines
• Stereochemical Studies. XLVI. Studies on the Synthesis of 4-Acetoxy-cyclopentane-1,3-dione Derivatives
• Stereochemical Studies. XLIV. Exploitation of the New Synthetic Scheme for Chiral Additives Usable in Asymmetric Syntheses. Novel Syntheses of optically Active γ-Amino Acids and Pyrrolidines from L-α-Amino Acids
• Stereochemical Studies. XLIII. Novel Reactivity of Organometallic Reagents to 5,5-Ethylenedioxy-2-methyl-2-phenylcyclohexanone
• Stereochemical Studies. XLII. Asymmetric Synthesis of naturally Occurring Podocarpic Acid
• Stereochemical Studies. XLI. Asymmetric Synthesis of optically Active 4a-Methyl-4,4a, 9,10-tetrahydro-2 (3H)-phenanthrone Derivatives, Key Intermediates for Total Syntheses of optically Active Diterpenes and Steroids
• Stereochemical Studies. XL. A Biomimetic Conversion of L-Lysine into optically Active 2-Substituted Piperidines. Syntheses of D- and L-Pipecolic Acid, and (S) (+)-Coniine from L-Lysine
• Stereochemical Studies. XXXIX. A Novel Method for the Preparation of Optically Active Aldehydes. Syntheses of Optically Active (R) (+)-α-Cyclocitral, (S) (+)-Dehydrovomifoliol, and (S) (+)-Abscisic Acid
• Stereochemical Studies. XXXV. A Biogenetic-type Asymmetric Cyclization. Syntheses of optically Active α-Cyclocitral and trans-α-Damascone
• Stereochemical Studies. XXXIV. A Novel Biogenetic-type Cyclization of Citral to α-Cyclocitral via an Enamine
• Stereochemical Studies. XXII. Thermal Rearrangement of S(-)-1-Phenylethyl Isocyanide
• Stereoselective Reactions. III. A highly Efficient Method for the Asymmetric Synthesis of 2-Alkylcycloalkanones via Chiral Chelated Lithioenamines
• Stereoselective Reactions. XXII. Design and Synthesis of Chiral Chelated Lithium Amides for Enantioselective Reactions
• REINVESTIGATION ON THE OPTICAL PURITIES OF OPTICALLY ACTIVE TRIMETHYLSILYL ENOL ETHERS OF 4-SUBSTITUTED CYCLOHEXANONES
• Biomimetic Studies Using Artificial Systems. VI. Design and Synthesis of Novel Cyclophanes Having Eight Carboxyl Groups on the Aromatic Rings
• A NOVEL WATER-SOLUBLE CYCLOPHANE AS A HOST FOR CATIONIC, ANIONIC, AND NEUTRAL AROMATIC GUESTS
• Chromatographic Separation of Armatic Guest Compounds by a Gel-Immobilized Water-Soluble Cyclophane
• Stereoselective Reactions. XIX. Asymmetric Dihydroxylation of Olefins by Employing Osmium Tetroxide-Chiral Amine Complexes
• The Chemistry of Diborane and Sodium Borohydride. XI. The Reaction of Isoquinoline Reissert Compounds with Sodium Borohydride
• Chemistry of Diborane and Sodium Borohydride. X. The Reduction of 2-or 4-Substituted Pyridines and Quinolines, and 1-or 3-Substituted Isoquinolines with Sodium Borohydride
• Chemistry of Diborane and Sodium Borohydride. IX. The Reduction of 3-Substituted Pyridines and Quinolines, and 4-Substituted Isoquinolines with Sodium Borohydride
• ENANTIOSELECTIVE DARZENS REACTION : ASYMMETRIC SYNTHESIS OF trans-GLYCIDIC ESTERS MEDIATED BY CHIRAL LITHIUM AMIDES
• Amino Acids and Peptides. II. A One-Step Synthesis of Atropine and Other Related Alkaloids from dl-Phenylalanine 3α-Tropanyl Ester
• Stereochemical Studies. XVII. Nitrous Acid Deaminations of (R)-α-Methylphenylalanine and Its Methyl Ester in Acetic Acid
• Stereoselective Reactions. XX. Synthetic Studies on Optically Active β-Lactams. III. Stereocontrolled Synthesis of Chiral Intermediate to (+)-Thienamycin from D-Glucose
• Stereoselective Reactions. XVIII. : Synthesis and Cytotoxicity of the Demethyl Derivatives of Steganes
• ASYMMETRIC α-ALKYLATION OF CYCLOHEXANONE BY MEDIATION OF A CHIRAL LIGAND AND THE LEAVING-GROUP EFFECT OF ELECTROPHILES ON ENANTIOSELECTIVITY
• Biomimetic Studies Using Astificial Systems. V. : Design and Synthesis of Novel Water-Soluble Bis-cyclophanes
• Stereoselective Reactions. XI. : Asymmetric Alkylation of Cyclohexanone via Chiral Chelated Lithioenamines Derived from D-Camphor Derivatives
• SYNTHETIC STUDIES TOWARD TRICHOTHECENE SESQUITERPENES. SYNTHESIS OF AN OPTICALLY PURE KEY INTERMEDIATE FOR CALONECTRIN USING HIGHLY STEREOSELECTIVE CYCLIZATION(Communications to the Editor)
• NOVEL BICYCLIC CHIRAL CROWN ETHERS HAVING A p-XYLENEDIOXY UNIT WITH INPROVED COMPLEX STABILITY AND RATE-ENHANCEMENT IN THE INTRA-COMPLEX THIOLYSIS OF α-AMINO ACID ESTER SALTS
• Stereoselective Reactions. V. Design of the Asymmetric Synthesis of Lignan Lactones. Synthesis of optically Active Podorhizon and Deoxypodorhizon by 1,3-Asymmetric Induction
• Biomimetic Studies Using Artificial Systems. II. Enantioselective Thiolysis of D- or L-α-Amino Acid Ester Salts by Thiol-Bearing Chiral Crown Ethers as an Enzyme Model
• Studies on Optically Active Amino Acids.XIII.Racemization of N-Benzoylanilides of Optically Active Proline and Pipecolic Acid
• Studies on Optically Active Amino Acids. XII.Synthesis, Resolution and Racemization of Bicyclic α-Amino-ketones
• Stereoselective Reactions. IX. Synthetic Studies on Optically Active β-Lactams. I. Chiral Synthesis of Carbapenam and Carbapenem Ring Systems Starting from (S)-Aspartic Acid
• SYNTHETIC STUDIES ON OPTICALLY ACTIVE β-LACTAMS. STEREOCONTROLLED SYNTHESIS OF CHIRAL THIENAMYCIN INTERMEDIATE FROM D-GLUCOSE
• Stereoselective Reactions. XII. : Synthesis of Antitumor-Active Steganacin Analogs, Picrosteganol and Epipicrosteganol, by Selective Isomerization
• Asymmetric Halolactonization Reactions. 3. Asymmetric Synthesis of optically Active Anthracyclinones
• Synthesis of Enantiomeric Pairs of Vicinal-Diols from L-α-Amino Acids by the Use of Organolithium Reagents : Its Application to optically Active Epoxyterpene Synthesis
• Synthesis of optically Active α-Alkyl or α-Aryl Acids from L-α-Amino Acids by the Use of Organocopper Reagents
• Functionalized Macrocycles. I. Synthesis of Thiol-bearing Crown Ethers as an Approach to Regioselective Catalysts
• Chemistry of Amino Acids. III. Reduction of Phenylalanine Ethyl Ester and Its Derivatives with Sodium Borohydride.
• Stereochemical Studies. XII. Effects of Neighboring Functional Groups on 1,2-Asymmetric Induction in the Reduction of Propiophenone Derivatives by Catalytic Hydrogenation
• Stereochemical Studies. XXXI. Total Synthesis of Several D-Pentose Derivatives. Stereochemical Courses of the Synthesis of Four Methyl 2,3-Anhydro-5-O-benzyl-D-pentofuranosides from L-Glutamic Acid and Their Reactions with Nucleophiles
• Stereochemical Studies. XVI. Deaminative Acetolyses of L-Valine and L-Valine Benzyl Ester
• Biomimetic Studies Using Artificial Systems. IV. : Biomimetic Peptide Synthesis by Using Multi-Functionalized Crown Ethers as a Novel Enzyme Model. A New Concept in Mimicking of Enzyme-Catalyzed Bond-Forming Reactions
• Amino Acids and Peptides. III. A New Synthetic Approach to N-Acylated α-Amino Aldehydes from N-Acylated α-Amino Acids by Catalytic Reduction of Their Mixed Carbonic-Carboxylic Acid Anhydrides with Palladium-Charcoal
• Stereochemical Studies. XV. Neighboring Aryl Group Participation in Nitrous Acid Deaminations of L-Phenylalanine and Its p-Nitro and p-Methoxy Derivatives. Conversion of L-Phenylalanine to naturally Occurring S-Tropic Acid
• Stereochemical Studies. XIV. Studies on the Neighboring Aryl Group Participation in Nitrous Acid Deaminations of L-Phenylalanine Ethyl Ester and Its p-Nitro and p-Methoxy Derivatives
• Stereochemical Studies. LII. Studies on the Stereochemical Courese in Deaminative Bromination of 3,5-Dichloro-L-tyrosine and in Amination of the Corresponding α-Bromo Acid. Existence of Strong Neighboring "Phenoxide"Group Participation
• Chemistry of Sodium Borohydride and Diborane. IV. Reduction of Carboxylic Acids to Alcohols with Sodium Borohydride through Mixed Carbonic-Carboxylic Acid Anhydrides
• Stereoselective Reactions. VIII. Stereochemical Requirement for the Benzylic Oxidation of Lignan Lactone. A Highly Selective Synthesis of the Antitumor Lignan Lactone Steganacin by the Oxidation of Stegane
• Stereoselective Reactions. VII. Synthesis of Racemic and Optically Pure Stegane, Isostegane, Picrostegane, and Isopicrostegane via Highly Selective Isomerization
• Stereoselective Reactions. X. Total Synthesis of Optically Pure Antitumor Lignan, Burseran
• Stereochemical Studies. L. Reductive Decyanization of α-Amino Nitriles with Sodium in Liquid Ammonia. An Alternate Method for the Application to the Asymmetric Synthesis of optically Active Natural Products
• Stereochemical Studies. XLIX. A Biogenetic-type Total Synthesis of Natural (+)-Maritidine from L-Tyrosine using highly Specific Asymmetric Cyclization
• Stereochemical Studies. XVIII. Nitrous Acid Deaminations of threo- and erythro-Phenylserine and Their Methyl Esters in Acetic Acid
• Stereochemical Studies. XI. Changes in the Stereochemical Course of 1,2-Asymmetric Induction in the Reduction of N-Substituted 2-Aminopropiophenone Derivatives with Sodium Borohydride
• Stereochemical Studies. X. Effects of Neighboring Functional Groups on 1,2-Asymmetric Induction in the Reduction of Propiophenone Derivatives with Sodium Borohydride

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