Synthetic Study of Tautomycin and Tautomycetin. Stereocontrolled Construction of the Dialkylmaleic Anhydride Segment
スポンサーリンク
概要
- 論文の詳細を見る
Strategies for the synthesis of a dialkylmaleic anhydride segment of tautomycin and tautomycetin are presented. The most difficult point was the stereocontrolled construction of the tetrasubstituted oletin. The maleate-type olefin construction through dehydration proved not to be adoptable because the corresponding β-hydroxyimine or aldol precursors were extremely unstable even under neutral conditions, suffering the retro-aldol-type decomposition. The Horner-Wadsworth-Emmons reaction on the α-ketoester with an appropriate protecting group had acceptable levels of diastereoselectivity giving rise to the dialkylmaleate diester, which was further led to the segment used in the synthesis of tautomycin and tautomycetin. In such the strategy, functional group protections were important in the olefination reaction and the final anhydride formation.
- 社団法人日本農芸化学会の論文
- 1995-11-23
著者
-
ICHIHARA Akitami
Department of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
-
OIKAWA Masato
Department of Chemistry, Graduate School of Science, Osaka University
-
OIKAWA Hideaki
Department of Applied Bioscience, Graduate School of Agriculture, Hokkaido University
-
Ueno Tohru
Department Of Bioscience And Chemistry Faculty Of Agriculture Hokkaido University
-
Ichihara A
Hokkaido Univ. Sapporo Jpn
-
Oikawa Masato
Department Of Bioscience And Chemistry Faculty Of Agriculture Hokkaido University
-
Ichihara Akitami
Department Of Applied Bioscience Graduate School Of Agriculture Hokkaido University
-
ICHIHARA Akitami
Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University
-
OIKAWA Hideaki
Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University
関連論文
- Novel Cyclohexene Compound from Lasiodiplodia theobromae IFO 31059
- Metabolism and Transport of [2-^C](±) Jasmonic Acid in the Potato Plant
- Four New Polyacetylenic Glucosides, Methyl β-D-Glucopyranosyl Helianthenate C-F, from Jerusalem Artichoke (Helianthus tuberosus L.)
- Tuber-forming Substances in Jerusalem Artichoke (Helianthus tuberosus L.)
- A Novel Sesquiterpene, Tuberonone, from Solanum tuberosum L.
- Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid
- Potent Inhibition of Macrophomate Synthase by Reaction Intermediate Analogs
- Macrophomate Synthase: Characterization, Sequence, and Expression in Escherichia coli of the Novel Enzyme Catalyzing Unusual Multistep Transformation of 2-Pyrones to Benzoates^1
- Efficient Degradation of Tautomycin to a Useful Synthetic Intermediate
- Novel Heinz Body Hemolysis Factors in Onion (Allium cepa)
- Synthesis and Potato Cell Expansion-inducing Activity of the Stereochemically Restricted Bicyclic Analogue of 7-Epi-jasmonic Acid
- Syntheses and Potato Tuber-inducing Activity of Coronafacic Acid Analogues
- Efficient Syntheses of the OPC Homologous Series, OPC-1:0, -3:0, -4:0, -5:0, -6:0, -7:0, and -8:0
- Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine
- Synthesis and Biological Activities of Lipid A Analogs Possessing β-Glycosidic Linkage at 1-Position
- Human MD-2 confers on mouse Toll-like receptor 4 species-specific lipopolysaccharide recognition
- Synthesis of[^3H]-Labeled Bioactive Lipid A Analogs and Their Use or Detection of Liped A-Binding Proteins on Murine Macrophages
- Conformational Study of a Tetraacyl Biosynthetic Precursor of Lipid A by NMR
- Identification of Branched Peptidic Structures that Recognize Immunostimulating Glycoconjugate Lipid A from Encoded Combinatorial Libraries
- An mRNA of Tobacco Cell, Which Is Rapidly Inducible by Methyl Jasmonate in the Presence of Cycloheximide, Codes for a Putative Glycosyltransferase
- Solanapyrones, Phytotoxins Produced by Alternaria solani : Biosynthesis and Isolation of Minor Components
- Chaetoglobosin O and Other Phytotoxic Metabolites from Cylindrocladium floridanum,a Causal Fungus of Alfalfa Black Rot Disease
- Synthesis of ^C-Labeled Biosynthetic Precursor of Lipid A and Its Analogue with shorter Acyl Chains
- A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues
- Synthesis of (S)-13-Hydroxy (2E,4E,8E)- and (2E,4E,8Z)-Tetradecatrienoic Acids
- Two Phenolic Compounds from Valsa ambiens
- Purification and N-Terminal Amino Acid Sequence of Solanapyrone Synthase, A Natural Diels-Alderase from Alternaria solani
- (-)-Semivioxanthin, A New Abscisic Active Compound against Hinoki Cypress Leaves Isolated from Cryptosporiopsis abietina
- New Efficient Synthesis of a Biosynthetic Precursor of Lipid A
- Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
- Yellow Fluorescent Stress Compounds, Pratenols A and B, from Red Clover (Trifolium pratense) Infected by Kabatiella caulivora
- Accumulation of Grisorixin Caused by Treating a Nigericin-producing Stain with a P-450 Inhibitor
- Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols
- Syntheses of Stereochemically Restricted Lactone-type Analogues of Jasmonic Acids
- Syntheses and Potato Tuber-inducing Activities of Unnatural Long-chain OPC-9 : 0 and OPC-10 : 0
- Syntheses of 3-Oxa-OPC and 2-Fluoro-OPC Homologues
- BIOLOGICAL ACTIVITIES OF PRECURSORS OF JASMONIC ACID AND THEIR ANALOGUES
- Synthetic Study of Tautomycin and Tautomycetin. Stereocontrolled Construction of the Dialkylmaleic Anhydride Segment
- Phytotoxic Metabolites Isolated from Scolecotrichum graminis Fuckel
- Chemical Structure of Lipid A from Helicobacter pylori Strain 206-1 Lipopolysaccharide
- 20-Ketoreductase Activity of Chaetoglobosin A and Prochaetoglobosins in a Cell-free System of Chaetomium subaffine and the Isolation of New Chaetoglobosins
- Inhibitory Effect of Coronamic Acid Derivatives on Senescence in Cut Carnation Flowers
- Practical Stereoselective Syntheses of All Four Stereoisomers of Coronamic Acid (2-Ethyl-1-aminocyclopropane-1-carboxylic acid)
- Purification and N-Terminal Amino Acid Sequence of Solanapyrone Synthase, A Natural Diels-Alderase from Alternaria solani
- Improved Synthesis of the C_8-C_ Segment of Aplysiatoxins via Asymmetric Dihydroxylation of the Chiral Homoallylic Alcohol
- Chemical Synthesis of Bacterial Glycoconjugates in Relation to Their Immunostimulating Activity
- Ferric Phosphate-dissolving Compound, Alfafuran, from Alfalfa (Medicago sativa L.) in Response to Iron-deficiency Stress
- (+)-Isocercosporin, A Phytotoxic Compound Isolated from Scolecotrichum graminis Fuckel(Organic Chemistry)
- Novel Acetamides Isolated from Scolecotrichum graminis Fuckel(Organic Chemistry)
- Biosynthesis of Phytotoxins from Alternaria solani
- Biosynthesis of Phytotoxins from Alternaria solani
- Re型リポ多糖の全合成
- B-5-4 Structure of Lampterol(Terpenoids)
- Bioorganic Chemistry of Alternaric Acid : Stereochemistry, Total Synthesis and Bioactivity
- Chemical Synthesis of Bacterial Glycoconjugates in Relation to Their Immunostimulating Activity
- The Structure of Zinnolide, a New Phytotoxin from Alternaria solani
- Synthesis of (±)-Epoxydon and Related Natural Compounds
- The Later Stage of the Biosynthesis of Aphidicolin: Accumulation of Intermediates with Cytochrome P-450 Inhibitors
- (3R, 5Z)-(-)-3-Hydroxy-5-dodecenoic Acid, A Phytotoxic Metabolite of Pythium ultimum
- Synthesis of Pyrenochaetic Acid A
- Absolute Configuration of Betaenone D as Determined by the CD Exciton Chirality Method
- Dihydrogladiolic Acid, another Phytotoxin from Phoma asparagi Sacc
- 3-Deoxyaphidicolin and Aphidicolin Analogues as Phytotoxins from Phoma betae
- Regioselective, abnormal ring opening of the epoxide of quinone epoxide-cyclopentadiene adducts.
- Synthesis of 5,5-Dimethyl-4-acetoxy-2-cyclopentenone, an Intermediate in the Total Synthesis of Illudin M, through Sulfur Compounds. A Novel Intramolecular Migration of Ethylenedioxy Group
- Stereospecific Reductions of Isoilludin S and M on Alumina Chromatography
- Enzymatic Synthesis of Lappaol B
- 3,3'-(Phenylphosphinylidene)bis(2(3H)-benzoxazolone) and 3,3'-(phenylphosphinylidene)bis(2(3H)-benzothiazolone). New activating agents.
- Isolation of Fulvic Acid from Cercospora beticola
- Synthesis of 5,5-Dimethyl-4-acetoxy-2-cyclopentenone and 5-Methyl-t-5-acetoxymethyl-r-4-acetoxy-2-cyclopentenone Intermediates for Illudin M and S
- A Phytotoxin, Betaenone C, and Its Related Metabolites of Phoma betae Fr
- Synthesis and Conformation of Cyclopropane Intermediates in the Total Synthesis of Illudin M and S
- N,N'-Carbonyldi(1,2-benzisoxazol-3(2H)-one): New, reactive condensing agent.