Synthesis of Two Possible Diastereoisomers of the Epoxy Lactone Proposed for Epoxyrollin A
スポンサーリンク
概要
- 論文の詳細を見る
Syntheses of two possible stereoisomeric epoxy lactones (20S,21R)- and (20R,21S)-1 that have been proposed for epoxy-rollin A, a structural representative of biosynthetic precursors of tetrahydrofuran annonaceous acetogenins, are described. Protected dihydroxy compound 4, which is the latent epoxy moiety of (20S,21R)- and (20R,21S)-1, was prepared by an 8-step sequence via Sharpless asymmetric dihydroxylation, starting from allyl alcohol 6. Preparation of γ-lactone moiety 5 was conducted by the method reported earlier. A palladium-catalyzed cross coupling reaction of 4 with 5 gave enyne 3, which, by a 3-step sequence, was converted into (20S,21R)- and (20R,21S)-1. The ^<13>C-NMR and mass spectraldata of the two synthetic diastereoisomers are not in accordance with those recorded for epoxyrollin A. Consequently, the structure of epoxyrollin A needs to be revised.
- 社団法人日本農芸化学会の論文
- 1995-12-23
著者
-
Araki T
Faculty Of Bioresources Mie University
-
Arai Takamitsu
Faculty Of Bioresources And Center For Molecular Biology And Genetics Mie University
-
KONNO HIROYUKI
Department of Surgery II, Hamamatsu University School of Medicine
-
Tanaka A
Faculty Of Bioresources Mie University
-
TANAKA Akira
Division of Medical Chemistry, National Institute of Hygienic Sciences
-
Konno Hiroyuki
Department Of Applied Biological Chemistry Faculty Of Agriculture
-
MAKABE Hidefumi
Department of Applied Biological Chemistry, Faculty of Agriculture
-
ORITANI Takayuki
Department of Applied Biological Chemistry, Faculty of Agriculture
-
Makabe H
Shinshu Univ. Nagano Jpn
-
Makabe Hidefumi
Department Of Applied Biological Chemistry Faculty Of Agriculture
-
Konno H
Univ. Tokushima Tokushima Jpn
-
Oritani T
Laboratory Of Applied Bioorganic Chemistry Division Of Bioscience & Biotechnology For Future Bio
-
Oritani Takayuki
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
-
Tanaka Akira
Division Of Biological Chemistry And Reference Standards National Institute Of Hygienic Sciences
関連論文
- Decontamination of Chlorate in Longan Plantation Soils by Bio-Stimulation with Sugar Amendment(Soil Biology)
- Cloning and Characterization of Phytochelatin Synthase from a Nickel Hyperaccumulator Thlaspi japonicum and Its Expression in Yeast
- Cloning and Characterization of Phytochelatin Synthase from a Nickel Hyperaccumulator Thlaspi japonicum and Its Expression in Yeast (Plant Nutrition)
- Differential Scanning Calorimetry of the Effects of Ca^ on the Thermal Unfolding of Pseudomonas cepacia Lipase(Biochemistry & Molecular Biology)
- Chemical Composition of Guttation Fluid and Leaves of Petasites japonicus v. giganteus and Polygonum cuspidatum Growing on Ultramafic Soil
- Esophageal Intramural Pseudodiverticulosis with Mallory-Weiss Syndrome : Report of a Case
- Gastrojejunocolic Fistula After Gastrectomy with Billroth II Reconstruction : Report of a Case
- Huge Cystic Lymphangioma of the Pancreas : Report of a Case
- Effect of Combination Therapy with Matrix Metalloproteinase Inhibitor MMI-166 and Mitomycin C on the Growth and Liver Metastasis of Human Colon Cancer
- Urokinase Receptor and Vascular Endothelial Growth Factor Are Synergistically Associated with the Liver Metastasis of Colorectal Cancer
- Prevention of Hepatic and Peritoneal Metastases by the Angiogenesis Inhibitor FR-118487 after Removal of Growing Tumor in Mice
- Combination Therapy with Vascular Endothelial Growth Factor Neutralizing Antibody and Mitomycin C on Human Gastric Cancer Xenograft
- Therapeutic Effect of 1 M Tegafur-0.4 M 5-Chloro-2,4-dihydroxypyridine-1 M Potassium Oxonate (S-1) on Liver Metastasis of Xenotransplanted Human Colon Carcinoma
- EFFECTS OF ROSE BENGAL ON SERUM LEVELS OF THYROID HORMONES AND THYROID PEROXIDASE ACTIVITY IN MALE MICE.
- Molecular Cloning, Characterization, and Expression Analysis of the xynF3 Gene from Aspergillus oryzae(Microbiology & Fermentation Technology)
- Molecular Cloning, Overexpression, and Purification of a Major Xylanase from Aspergillus oryzae
- Analysis of the Promoter Activity of the Taka-Amylase Gene and the Phosphoglycerate Kinase Gene in a Shoyu-koji Mold Aspergillus oryzae KBN616
- Synthesis and Biological Activity of New Water-soluble Cytokinins
- Synthesis of Squamostanal-A
- Synthesis of Two Possible Diastereoisomers of the Epoxy Lactone Proposed for Epoxyrollin A
- P-364 Total Synthesis of Murisolin, Murisolin A, and 16,19-cis-Murisolin
- Crohn's Disease of the Esophagus : Report of a Case
- Enhanced Growth and Nodule Occupancy of Red Kidney Bean and Soybean Inoculated with Soil Aggregate-Based Inoculant
- Improved Survival of Nutrient-Starved Cells of Rhizobium tropici CIAT899 in Acid Soil Associated with High AI^ and Mn^ Contents
- Free Radical Injury in Rice Leaf under Zn Deficiency
- Characterization of Mycorrhizas Formed by Glomus sp. on Roots of Hypernodulating Mutants of Lotus japonicus
- Isolation of Two Different Phenotypes of Mycorrhizal Mutants in the Model Legume Plant Lotus japonicus after EMS-Treatment
- Simple Method of Genomic DNA Extraction from Rhizobia in Dried Nodules of Phaseolus vulgaris for Strain Differentiation by PCR-Based DNA Fingerprinting
- 8-18 Effect of nutrient starvation on survival, stress resistance and competitive nodulation ability of Rhizobium tropici CIAT899.
- 8-9 The influence of mycorrhizal colonization on condensed tannin synthesis in root and shoot of Lotus japonicus.
- Basic Subsite Theory Assumptions May Not Be Applicable to Hydrolysis of Cellooligosaccharides by Almond β-Glucosidase
- Changes in the Level of Protein and Activity of Cu/Zn-Superoxide Dismutase in Zinc Deficient Rice Plant, Oryza sativa L.
- Intracystic Hemorrhage of Pancreatic Serous Cystadenoma After Renal Transplantation: Report of a Case
- Regression of Metastatic Liver Tumors in Rats Treated with Angiogenesis Inhibitor TNP-470 : Occurrence of Apoptosis and Necrosis
- Synthesis and Structure Activity Relationship Studies of Miraziridine A, a Cysteine Protease Inhibitor
- Synthetic Studies on Miraziridine A, a Cysteine Protease Inhibitor Isolated from Theonella aff. mirabilis
- P-61 SYNTHESES OF TOKARAMIDE A AND MIRAZIRIDINE A CYSTEINE PROTEASE INHIBITORS FROM THEONELLA AFF. MIRABILIS
- Synthetic Studies of Tokaramide A and Miraziridine A Isolated from Marine Sponge Theonella aff. mirabilis
- Molecular Cloning and Analysis of the 5'-Flanking Region of the Human Thiamin Pyrophosphokinase Gene
- Fast Parameter Selection Algorithm for Linear Parametric Filters(Digital Signal Processing)
- 2P-079 グルコアミラーゼのデンプン結合ドメインの安定性とリフォールディング過程に対するジスルフィド結合の効果(蛋白質・物性(2),第46回日本生物物理学会年会)
- A Unified Framework of Subspace Identification for D.O.A. Estimation(Engineering Acoustics)
- The Family of Regularized Parametric Projection Filters for Digital Image Restoration
- Fe^(bipyridine)_3-Complex : A Novel Tool for Conformational Studies of Collagen
- Steady-State Inhibitory Kinetic Studies on the Ligand Binding Modes of Aspergillus niger Glucoamylase
- Guanidine Hydrochloride-Induced Denaturation of Pseudomonas cepacia Lipase
- Possibility for Discriminating Between Two Representative Non Two-state Thermal Unfolding Models of Proteins by DSC
- Thermal Unfolding of the Starch Binding Domain of Aspergillus niger Glucoamylase
- Isothermal Titration Calorimetric Studies on the Binding of a Family 6 Carbohydrate-binding Module of Clostridium thermocellum XynA with Xlylooligosaccharides(Biochemistry & Molecular Biology)
- Cloning, DNA Sequencing, and Expression of the β1,4-Mannanase Gene from a Marine Bacterium, Vibrio sp. Strain MA-138
- Sequence of the Clostridium thermocellum Mannanase Gene man26B and Characterization of the Translated Product
- Antimetastatic Effect of Hepatotropic Liposomal Adriamycin on Human Metastatic Liver Tumors
- Intrahepatic cholangiojejunostomy for unresectable malignant biliary tumors with obstructive jaundice
- Lymphoepithelial Cyst of the Pancreas : Report of a Case
- Marginal ulceration after pylorus-preserving pancreaticoduodenectomy
- Synthesis of a Tricyclo[4.3.0.0^]-nonane Ring System from (-)-Carvone(Organic Chemistry)
- Synthesis of (+)-Methyl Phaseate and Its Isomer from (-)-β-Pinene(Organic Chemistry)
- Total Synthesis of (+)-Methyl Phaseate from (-)-β-Pinene(Organic Chemistry)
- Total Synthesis of (±)-Drummondone A(Organic Chemistry)
- Alternative Synthesis of (±)-Trisporol B via (±)-6-Hydroxymethyl-2,6-dimethyl-2-cyclohexen-1-one(Organic Chemistry)
- Synthesis and Biological Activities of (±)-Deoxy-abscisic Acid Isomers
- Total Synthesis of (±)-Methyl Phaseates(Organic Chemistry)
- Purification and Some Properties of Alkaline Proteinases from Cephalosporium sp. KM388(Biological Chemistry)
- Synthesis of Chiral Aspyrone, A Multi-functional Dihydropyranone Antibiotic
- Total Synthesis of Natural (+)-Phomopsolide B, an Antifeedant against Elm Bark Beetle
- Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid(Organic Chemistry)
- Enzymatic Preparation of Chiral 4-Hydroxy-2,2-dimethyl-1-cyclohexanone as a Chiral Building Block(Organic Chemistry)
- Syntheses and Biological Activities of (±)-Streptovitacin A and E-73(Organic Chemistry)
- Synthesis of (±)-4'-Hydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid(Organic Chemistry)
- Synthesis of (±)-(2Z,4E)-trans-1',4'-Dihydroxy-γ-ionylideneacetic Acid, a Fungal Biosynthetic Intermediate of Abscisic Acid(Organic Chemistry)
- Synthesis of Chiral 3'-Hydroxy-γ-ionylideneacetic Acids (Organic Chemistry)
- Synthesis and Biological Activities of Demethylcycloheximides(Organic Chemistry)
- Preparation of Chiral trans-2,4-Dimethyl-1-cyclohexanones, the Key Intermediates in Cycloheximide Synthesis, Using Microbial Resolution(Organic Chemistry)
- Efficient Synthesis of Akolactone A via Pd-Catalyzed Carbonylation(Organic Chemistry)
- Structural Revision of Epoxyrollins A and B, Biosynthetic Precursors of Annonaceous Acetogenins(Organic Chemistry)
- Bohr's Search for the Quantum Theory of Dispersion : The Number of Dispersion Electrons, Absorption and Emission of Light and the Oscillator Model
- Substrate Specificity of Alkaline Proteases from Cephalosporium sp. KM388
- Ice Nuclei Produced by Fusarium sp. Isolated from the Gut of the Rice Stem Borer,Chilo suppressalis WALKER (Lepidoptera : Pyralidae)
- Effect of Family 22 Carbohydrate-Binding Module on the Thermostability of Xyn10B Catalytic Module from Clostridium stercorarium
- Disposition and Metabolism of 2-Nitro-p-cresol in Rats and Its Effect on Hepatic Ornithine Decarboxylase (Proceedings of the 12 th Symposium on Environmental Pollutants and Toxicology) (Regular Presentations)
- Synthetic Studies on Callipeltins B and E Isolated from Marine Sponge
- 2-Fluoro and 2-Methoxycarbonyl Epoxy-β-ionylideneacetic Acids as Abscisic Acid Analogs
- Thermal Unfolding and Modular Architecture of Clostridium stercorarium Xyn10B
- Process of Thermal Denaturation of Xylanase (XynB) from Clostridium stercorarium F-9
- Synthesis of (-)-Muricatacin
- Purification and Properties of Extracellular Carboxyl Proteinase Secreted by Candida pulcherrima
- Thermal Unfolding and Modular Architecture of Clostridium stercorarium Xyn10B
- Puritication and Properties of α-Glucosidase from Trichoderma viride
- Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S, 4aS, 8S)-4a, 8-Dimethyl-2,3,4,4a, 5,6,7,8-octahydro-2-naphthalenol
- Synthetic study of callipeltin A, an anti-HIV cyclic depsipeptide isolated from marine sponge
- Synthesis of Annonacin Isolated from Annona densicoma
- Synthesis and Evaluation of Small Peptide Inhibitors for SARS 3CL Protease
- Slater's Theory of Line Breadth and the Virtual Oscillator Model : A Premature Attempt in the Old Quantum Theory
- Application of the AMeX method to the evaluation of HER-2 status in breast carcinomas: Comparison with the results of HercepTest
- New Host Records of Ichneumonidae(Hymenoptera), with Description of a New Eriborus Species from Japan(VIII)
- Search for Lens-Aldose-Reductase Inhibitor in Medicinal Plants
- Synthetic Study of the Depsipeptides Analogues of Callipeltin B and Its Cytotoxicity
- Evaluation of Inhibitory Activities of Curcumin Derivatives Using BACE1 and Amyloid Beta Peptide
- Synthesis of Bioactive Natural Products as Protein Inhibitors
- Synthesis of BK-1097 Analogues and Evaluation of Antifungal Activity