Diastereoselective Synthesis of (2R, 4R)-2-Aryl-4-hydroxypyrrolidine : Preparation of the Side Chain of Novel Carbapenem

スポンサーリンク

概要

• 論文の詳細を見る

• Improved synthesis of the trans-3, 5-disubstituted pyrrolidin-3-ylthio side-chain of the novel carbapenem 1 was achieved via stereoselective reduction of the 1-aryl-1-butanone derivative 5 and successive intramolecular cyclization of the resulting chiral alcohol 6. The 1-aryl-1-butanone derivative 5 was obtained by a coupling reaction of protected 4-hydroxy-2-pyrrolidone with aryl-Grignard reagent.

• 公益社団法人日本薬学会の論文
• 2001-11-01

著者

• SATO Hiromi

  Tohoku College of Pharmacy

• Hirose M

  Banyu Tsukuba Research Institute

• HASHIHAYATA Takashi

  Banyu Tsukuba Research Institute

• SAKOH Hiroki

  Banyu Tsukuba Research Institute

• GOTO Yasuhiro

  Banyu Tsukuba Research Institute

• HIROSE Masaaki

  Banyu Tsukuba Research Institute

• SAKURABA Shunji

  Banyu Tsukuba Research Institute

• IMAMURA Hideaki

  Banyu Tsukuba Research Institute

• SUGIMOTO Yuichi

  Banyu Tsukuba Research Institute

• YAMADA Koji

  Banyu Tsukuba Research Institute

• MORISHIMA Hajime

  Banyu Tsukuba Research Institute

• Sato H

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• GOTO Yuki

  Faculty of Environmental and Symbiotic Sciences, Prefectural University of Kumamoto

• Sugimoto Yoshikazu

  Hanno Research Center Taiho Pharmaceutical Co. Ltd.

• Yamada K

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Goto Yuki

  Faculty Of Environmental And Symbiotic Sciences Prefectural University Of Kumamoto

• Yamada Katsuya

  Graduate School Of Pharmaceutical Sciences Nagoya City University

• Sakuraba S

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Sugimoto Yuichi

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Sakoh H

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• HASHIHAYATA Takashi

  Center for Basic Research, The Kitasato Institute (TCI)

• Morishima H

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Hashizume T

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

• Hashihayata T

  Center For Basic Research The Kitasato Institute (tci)

• Imamura H

  Banyu Tsukuba Research Institute Banyu Pharmaceutical Co. Ltd.

関連論文

• Activation of the Human Ah Receptor by Aza-Polycyclic Aromatic Hydrocarbons and Their Halogenated Derivatives
• Synthesis of Fluorine Analogues of Protoporphyrin Potentially Useful for Diagnosis and Therapy of Tumors
• Nucleophilic Substitution Reaction in Indole Chemistry: 1-Methoxy-6-nitroindole-3-carbaldehyde as a Versatile Building Block for 2,3,6-Trisubstituted Indoles
• Synthesis of Nb-acyltryptamines and their 1-hydroxy-tryptamine derivatives as new α2-blockers
• Isolation and Absolute Structures of the Neolignan Glycosides with the Enantimetric Aglycones from the Leaves of Viburnum awabuki K. KOCH
• Diastereoselective Synthesis of (2R, 4R)-2-Aryl-4-hydroxypyrrolidine : Preparation of the Side Chain of Novel Carbapenem
• Synthesis of a Key Intermediate of Novel Galbonolide Analogues via Efficient Construction of a Conjugated Diene System
• Synthesis and Antifungal Activity of Novel 14-Membered Benzomacrolides, as Galbonolide Analogues
• Synthesis of the Side Chain of a Novel Carbapenem via Iodine-Mediated Oxidative Cyclization of (1R)-N-(1-Aryl-3-butenyl)acetamide
• Practical Synthesis of a 1β-Methylcarbapenem, J-111, 225, Using 4-Mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine as a Precursor
• A Novel 1β-Methylcarbapenem, J-111,225 : Effects of the C-3 and C-5 Stereochemistry of the Pyrrolidinylthio Side Chain on Antibacterial Activities
• Expression of Membrane-Type 1 Matrix Metalloproteinase (MT1-MMP) mRNA in Trophoblast and Endometrial Epithelial Cell Populations of the Synepitheliochorial Placenta of Goats (Capra hircus)
• Cell-Cell Contract Down-Regulates Expression of Membrane Type Metalloproteinase-1 (MT1-MMP) in a Mouse Mammary Gland Epithelial Cell Line
• Structure-Activity Relationship Studies on the Novel Neuropeptide Orexin
• Characterization of Fe(III)-Deferoxamine and Mn(II)-Pectin as Magnetic Resonance Imaging Contrast Agents
• New Cdc25B Tyrosine Phosphatase Inhibitors, Nocardiones A and B, Produced by Nocardia sp. TP-A0248 : Taxonomy, Fermentation, Isolation, Structural Elucidation and Biological Properties
• Reactions of 1-Methoxy-3-(2-nitrovinyl)indole with Nucleophiles: An Interesting Solvent Effect and a Novel Preparation of 3-Substituted 1-Methoxyindoles
• The Chemistry of Indoles.CVII.A Novel Synthesis of3, 4, 5, 6-Tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles and a New Finding on Pictet-Spengler Reaction
• The Chemistry of Indoles.CIII.^ Simple Syntheses of Serotonin, N-Methylserotonin, Bufotenine, 5-Methoxy-N-methyltryptamine, Bufobutanoic Acid, N-(Indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and Lespedamine Based on 1-Hydroxyindole Chemistry
• Conjugated Linoleic Acid Reduces Body Fats and Cytokine Levels of Mice(Food & Nutrition Science)
• Dietary Manipulations of Body Fat-reducing Potential of Conjugated Linoleic Acid in Rats(Food & Nutrition Science)
• Cytochrome P450 2E1/2A6-Selective Inhibition by Halogenated Anilines on Metabolic Activation of Dimethylnitrosamine in Human Liver Microsomes
• Inhibition of Human Cytochrome P450 2E1 by Halogenated Anilines, Phenols, and Thiophenols(Medicinal Chemistry)
• Expression of Matrix Metralloproteinase-11 (Stromelysin-3) and TIMP-1 Genes in the Placenta and the Uterus during Estrous Cycles and Gestation in the Mouse
• A novel cinnamic acid derivative that inhibits Cdc25 dual-specificity phosphatase activity
• Effect of 2,5-Dimethylpyrazine on Uterine Contraction in Late Stage of Pregnant Female Rats(Pharmacology)
• An Asymmetric Synthesis of the ABC Ring System of 8-Demethyltaxoids from Optically Active 8-Membered Ring Compound via Intramolecular Aldol and Pinacol Coupling Reactions
• An Asymmetric Synthesis of the BC Ring System of 8-Epitaxoids by Way of Intramolecular Aldol and Successive Stereoselective Methylation Reactions
• Isolation and Structure of a Galactocerebroside from the Sea Cucumber Bohadschia argus
• Isolation and Structure of a Monomethylated Ganglioside Possessing Neuritogenic Activity from the Ovary of the Sea Urchin Diadema setosum
• Biologically active gangliosides from echinoderms
• Determination of the Absolute Configuration of Sialic Acids in Gangliosides from the Sea Cucumber Cucumaria echinata
• Neuritogenic Activity of Gangliosides from Echinoderms and Their Structure : Activity Relationship
• Constituents of Holothuroidea, 18. Isolation and Structure of Biologically Active Disialo- and Trisialo-Gangliosides from the Sea Cucumber Cucumaria echinata
• Constituents of Holothuroidea, 17. Isolation and Structure of Biologically Active Monosialo-Gangliosides from the Sea Cucumber Cucumaria echinata
• Solvent effect on the reaction of 1-methoxy-3-(2-nitrovinyl)indole with nucleophiles
• Constituents of Holothuroidea, 16. : Determination of Absolute Configuration of the Branched Methyl Group in Ante-iso Type Side Chain Moiety on Long Chain Base of Glucocerebroside from the Sea Cucumber Holothuria leucospilota
• Constituents of Holothuroidea, 15 : Isolation of Ante-iso Type Regioisomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota
• Constituents of Holothuroidea, 14. Isolation and Structure of New Glucocerebroside Molecular Species from the Sea Cucumber Stichopus japonicus
• Novel syntheses of 1-hydroxy-6- and -5-nitroindole-3-carbaldehydes, and their derivatives as daikon-phytoalexin analogs
• Constituents of Holothuroidea, 13. Structure of Neuritogenic Active Ganglioside Molecular Species from the Sea Cucumber Stichopus chloronotus
• Nucleophilic substitution reactions of 1-methoxy-6-nitroindole-3-carbaldehyde 1
• Constituents of Holothuroidea, 12. Isolation and Structure of Glucocerebrosides from the Sea Cucumber Holothuria pervicax
• Synthesis of analogs of wasabi phytoalexin (methyl 1-methoxyindole-3-carboxylate)
• Herpes simplex virus-induced, death receptor-dependent apoptosis and regression of transplanted human cancers
• Inhibitory Effect of 2,5-Dimethylpyrazine on Oxytocic Agent -induced Uterine Hypercontraction of Normal or Pregnant Female Rats
• Synthesis of J-111,347,a Novel 1β-Methylcarbapenem with Broad-spectrum Antibacterial Activity
• Effects of Benzyl Glucoside and Chlorogenic Acid from Prunus mume on Adrenocorticotropic Hormone (ACTH) and Catecholamine Levels in Plasma of Experimental Menopausal Model Rats(Pharmacognosy)
• Effects of Benzyl Glucoside and Chlorogenic Acid from Prunus mume on Angiotensin Converting Enzyme, Aldosterone and Corticosterone Levels in Rat Plasma
• Inhibitory Effects of Benzyl Glucoside and Chlorogenic Acid from Prunus mume on Bradykinin and Prostaglandin E_2 Production in the Abdominal Cavities of Mice
• Synthesis of 18-Demethyltaxoid via Stereoselective Allylation and Intramolecular Aldol Condensation Reactions
• Estimation of Distribution of p-Hydroxybenzoic Acid Esters between Non-ionic Surfactant Micellar and Aqueous Phases
• Interaction between Hydroxybenzoic Acid Esters and Polyoxyethylene Cetyl Ether
• Aggregate Formation of p-Hydroxybenzoic Acid Esters in Aqueous Solution
• Effects of Added Lower Alcohols on Solubilized Tocopherol Acetate Sorption to Polyethylene Film in Aqueous Solution
• Constituents of Holothuroidea.10.^Isolation and Structure of a Biologically Active Ganglioside Molecular Species from the Sea Cucumber Holothuria leucospilota
• In vivo Anti-tumor Activity of a Novel Indolocarbazole Compound, J-107088, on Murine and Human Tumors Transplanted into Mice
• Antipyretic Activity of Gingyo-san, a Traditional Medicine, in Influenza Virus-Infected Mice
• Bacterial Susceptibility to Butyl ρ-Hydroxybenzoate in the Presence of Polyoxyethylene Cetyl Ether
• Effects of Polyoxyethylene Cetyl Ether on the Cellular Uptake and Antibacterial Activity of Butyl ρ-Hydroxybenzoate against Escherichia coli
• Efficacy of Kampo medicines on cutaneous herpes simplex virus type 1 infection in mice
• Effects of the Structures of Polyoxyethylene Alkyl Ethers on Uptake of Butyl p-Hydroxybenzoate by Escherichia coli and Its Antibacterial Activity
• Efficacy of Cafon gel on cutaneous infection with herpes simplex virus (HSV)-2 and acyclovir-resistant HSV in mice
• Relationship between Uptake of p-Hydroxybenzoic Acid Esters by Escherichia coli and Antibacterial Activiy
• Expression of Matrix Metalloproteinase-11 (Stromelysin-3) and TIMP-1 Genes in the Placenta and the Uterus during Estrous Cycles and Gestation in the Mouse
• A New Method for the Synthesis of Baccatin III
• Stereocontrolled Synthesis of the BC Ring System of Taxol
• Expression of Matrix Metalloproteinase-11 Genes in Placentae and Uteri of Shiba Goats (Capra hircus)
• Isolation and Structure Determination of cerebrosides from Garlic, the Bulbs of Allium sativum L.
• Scandium(III) Perfluorooctanesulfonate [Sc(OPf)_3]: A Novel Catalyst for the Hetero Diels-Alder Reaction of Aldehydes with Non-Activated Dienes
• A MNDO-PM3 STUDY ON THE SELECTIVE ACTIVATION OF l-O-METHOXYACETYL SUGARS BY ZINC(II) OR YTTEBRIUM(III) ION
• Metal-Containing Components in Medicinal Plants. III.Manganese-Containing Components in Theae Folium as Oral Magnetic Resonance Imaging Contrast Materials
• 6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations
• Catalytic and β-Stereoselective Mannosylation of Several Glycosyl Acceptors with Mannosyl 6-Nitro-2-benzothiazoate
• Glycosyl 6-Nitro-2-benzothiazoate. A Highly Efficient Donor for β-Stereoselective Glycosylation
• A novel methodology for preparing 5-chloro- and 5-bromotryptamines and tryptophans, and its application to the synthesis of (±)-bromochelonin B
• Simple syntheses of analogs of a wasabi phytoalexin
• Convergent Total Syntheses of Oligosaccharides by One-Pot Sequential Stereoselective Glycosylations
• Convergent and Convenient Total Synthesis of Phytoalexin-Elicitor Active Heptasaccharide by One-Pot Sequential Glycosylation
• A Convergent Total Synthesis of the Mucin Related F1α Antigen by One-Pot Sequential Stereoselective Glycosylation
• Constituents of Holothuroidea.9. Isolation and Structure of a New Ganglioside Molecular Species from the Sea Cucumber Holothuria pervicax
• Biotransformation of D-Xylulose to D-Xylose by Immobilized Enzyme Prepared from Streptomyces flavorirensis
• Simple syntheses of indol-1-yl glucosides
• Constituents of Viburnum awabuki(Natural Medicine Note)
• Effects of Benzyl Glucoside and Chlorogenic Acid from Prunus mume on Angiotensin Converting Enzyme, Aldosterone and Corticosterone Levels in Rat Plasma
• Inhibitory Effects of Benzyl Glucoside and Chlorogenic Acid from Prunus mume on Bradykinin and Prostaglandin E_2 Production in the Abdominal Cavities of Mice
• Isolation of Benzyl Glucoside and Chlorogenic Acids from the Fruits of Prunus mume(Natural Medicine Note)
• Social Skills Training for Children

もっと見る 閉じる

スポンサーリンク