Asymmetric Synthesis of β-Hydroxy Acid via Stereoselective Dirhodium (II)-Catalyzed C-H Insertion of α-Alkoxydiazoketone
スポンサーリンク
概要
- 論文の詳細を見る
A new methodology for the asymmetric synthesis of β-hydroxy acid was developed. Dirhodium (II)-catalyzed C-H insertion of α-alkoxydiazoketone (3), which was prepared from primary alkyl halide (I) and readily available chiral Gf-hydroxy acid (2), gave stereoselectively 2,5-cis-disubstituted 3(2H)-furanone (4). The Baeyer-Villiger reaction of 4 followed by treatment with an acid afforded chiral β-hydroxy acid (6) with high optical purity.
- 公益社団法人日本薬学会の論文
- 2003-04-01
著者
-
Tanaka T
Osaka Univ. Osaka Jpn
-
田中 恒雄
Department Of Pharmacy Hyogo College Of Medicine
-
YAKURA Takayuki
Kyoto Pharmaceutical University
-
IKEDA Masazumi
Kyoto Pharmaceutical University
-
Tamura Y
Kyoto Pharmaceutical University
-
TANAKA Takeshi
Kyoto Pharmaceutical University
-
Uenishi J
Kyoto Pharmaceutical University
関連論文
- Synthetic Studies on Aphidicolane and Stemodane Diterpenes. IV.A Stereoselective Formal Total Synthesis of (±)-Aphidicolin
- Synthetic Studies on Aphidicolane and Stemodane Diterpenes. III.An Alternative Stereoselective Access to Aphidicolane-Type B/C/D-Ring System
- 61 アフィディコラン型およびステモダン型ジテルペンの合成研究(ポスター発表の部)
- Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.0^]dodecanes Corresponding to the B/C/D-Ring Systems
- Synthetic Studies on Spiroketal Natural Products. V. Total Synthesis of (+)-Talaromycin A and (-)-talaromycin B
- Synthetic Studies on Spiroketal Natural Products. IV.A Stereoselective Synthesis of (3S, 5S, 6R, 9R, R_S)-3-Benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro[5.5]undecane, a Key Intermediate for Talaromycins
- Flavonol Glycosides in Leaves of Two Diospyros Species
- 102(P-59) (±)-Scopadulinの全合成(ポスター発表の部)
- 131(P-78) 抗腫瘍活性アセトゲニンMosin Bの不斉合成研究(ポスター発表の部)
- 多官能性化合物2- (N-シアノイミノ) チアゾリジン誘導体の合成化学的活用
- 50(P10) Macrocarpal類の不斉合成研究(ポスター発表の部)
- Synthetic Studies on Aphidicolane and Stemodane Diterpenes. V. A Facile Formal Total Synthesis of (±)-Aphidicolin via a Lewis Acid-Mediated Stereoselective Spiroannelation
- Lewis Acid-Mediated Stereoselective Spiroannelation : A Facile Access to Aphidicolane and Stemodane B/C/D Ring Systems
- P-18 (+)-Perhydrohistrionicotoxinの合成(ポスター発表の部)
- Synthetic Studies on Aromadendrane-Type Compounds. II.Stereoselective Synthesis of (+)-1,2-Didehydroaromadendrane
- Synthetic Studies on Aromadendrane-Type Compounds. I. Stereoselective Construction of Aromadendrane- and Alloaromadendrane-Type Skeletons
- Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt
- Synthetic Study on Gymnomitrol. II. A Synthesis of (±)-Isogymnomitrol
- 57 アロマデンドラン型化合物の不斉合成研究(ポスター発表の部)
- Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1,2,6-Trimethyltetracyclo[5.3.1.0^.0]undecan-9-one
- 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. VI. An Improved Formal Synthesis of (±)-Descarboxyquadrone via Highly Regioselective Cyclopropane Ring Opening of Tricyclo[3.3.0.0^]octan-3-one
- Synthetic Studies on Securitinine and Related Compounds. I. Stereochemistries of the Catalytic Hydrogenation Products of 6-(4-Methoxy-2-pyridyl)-1,4-dioxaspiro [4,5] decan-6-ol
- 93(P-22) 抗腫瘍活性アセトゲニン類の系統的不斉合成法の開発 : Murisolinの不斉合成への応用(ポスター発表の部)
- P-448 STRUCTURES OF STILBENE OLIGOMERS IN DIPTEROCARPACEAEOUS PLANTS
- New resveratrol oligomers in the stem bark of Vatica pauciflora
- Six New Heterocyclic Stilbene Oligomers from Stem Bark of Shorea hemsleyana.
- Five New Oligostilbenes with One or Two Dihydrofurans form the Stem Bark of Vatica rassak.
- A Novel Bridged Stilbenoid Trimer and Four Highly Condensed Stilbenoid Oligomers in Vatica rassak.
- Synthesis of 7-Thiaprostaglandin E_1 Congeners : Potent Inhibitors of Platelet Aggregation
- Synthesis of Thiaprostaglandin E_1 Derivatives
- SYNTHESIS OF NEW ANTINEOPLASTIC ALKYLIDENECYCLOPENTENONES
- SYNTHESIS OF NEW ANTINEOPLASTIC PROSTAGLANDINS
- TOTAL SYNTHESES OF STABLE PGI_2 DERIVATIVES : SYNTHESES OF 7-HYDROXY-AND 7-FLUORO-PGI_2
- Synthesis of New Secoprostaglandins as Inducers of Platelet Aggregation
- Platelet Anti-aggregant Activity of 2,2-Dimethylthiazolidine Hydrochloride and 2-(4-Hydroxy-3-methoxyphenyl)thiazolidine
- A FORMAL TOTAL SYNTHESIS OF (±)-QUADRONE
- Synthetic Studies on Acorane-Alaskane Sesquiterpenes. I. Total Synthesis of (±)-β-Acorenol
- 40 Acorane-Alaskane型セスキテルペンの合成研究
- Melanogenesis Stimulation in Murine B16 Melanoma Cells by Kava (Piper methysticum) Rhizome Extract and Kavalactones(Pharmacognosy)
- Asymmetric Desymmetrization of Prochiral 1,3-Diols via Diastereoselective C-O Bond Fission of Bicyclic Acetal Using a Chiral Sulfoxide as a Chiral Auxiliary
- 4-(2-Aminoethylamino)-7H-benz[de]benzimidazo[2,1-a]isoquinoline-7-one as a Highly Sensitive Fluorescent LabelingReagent for Carnitine
- Antibacterial Activity of Stilbene Oligomers against Vancomycin-Resistant Enterococci (VRE) and Methicillin-Resistant Staphylococcus aureus (MRSA) and Their Synergism with Antibiotics
- A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa
- Stilbene Oligomers in Roots of Sophora moorcroftiana
- Stilbene Derivatives from Two Species of Gnetaceae
- Four New Glucosides of Stilbene Oligomers from theStem of Gnetum gnemonoides
- Stilbenoids in Lianas of Gnetum parvifolium
- Three New Trimeric Stilbenes from Gnetum gnemon
- Four New Glucosides of Stilbene Oligomers From the Stem of Gnetum gnemonoides.
- Inhibitory Effect of Plant Extracts on Production of Verotoxin by Enterohemorrhagic Escherichia coli 0157 : H7.
- SYNTHESIS OF NEW SULFUR-CONTAINING PROSTAGLANDIN I_1
- Revised Structure of Cercidinin A, a Novel Ellagitannin Having (R)-Hexahydroxydiphenoyl Esters at the 3, 4-Positions of Glucopyranose
- A Formal Total Synthesis of (-)-Cephalotaxine
- Approaches to the Cephalotaxine Skeleton Using an Intramolecular Heck Reaction
- Photolysis of Alkynyl(phenyl)iodonium Salts. Remarkable Solvent Effect and Generation of Acids
- Factors Affecting the Dissolution Rate of Sulpiride from Tablets Coated with Polyvinylacetal Diethylaminoacetate, a Gastric-Fluid-Soluble Polymer. II. Effect of Mechanical Destructive Force and Film Coating Strength in the Gastrointestinal Tract
- Potent NK_1 Receptor Antagonists : Synthesis and Antagonistic Activity of Various Heterocycles with an N-[3,5-Bis(trifluoromethyl)benzyl]-N-methylcarbamoyl Substituent
- Synthetic Studies on Spirovetivane Phytoalexins. III. : A Total Synthesis of (±)-Lubiminol
- Synthetic Studies on Spirovetivane Phytoalexins. II. : Stereoselective Synthesis of (2RS, 5RS, 6SR, 8RS, 10SR)-6-Hydroxymethyl-8-methoxymethoxy-10-methyl-2-pivaloyloxyspiro[4.5]decane
- Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. : Total Synthesis of (±)-Acorenone
- 16 Spirovetivane型Phytoalexin類の合成研究 : (±)-Lubiminolおよび(±)-oxylubiminの立体選択的全合成
- Resveratrol Tetramers with a C_6-C_3 or a C_1 Unit from Upuna borneensis
- Resveratrol Oligomers and Their O-Glucosides from Cotylelobium lanceolatum
- A New and Known Cytotoxic Aryltetralin-Type Lignans from Stems of Bursera graveolens
- Resveratrol Derivatives from Upuna borneensis
- Three New Trimeric Stilbenes from Gnetum gnemon.
- Six Flavonostilbenes from Gnetum africanum and Gnetum gnemon
- 7,7-Dimethyltricyclo[3.3.0.0^]octan-r-ones as Synthetic Intermediates. V. : An Improved Synthesis of (±)-Pentalenene
- 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. IV. : A Further Examination of Cyclopropane Ring Opening in the Tricyclo[3.3.0.0^]octan-3-one System
- Inhibition of Preadipocyte Differentiation by Germacranolides from Calea urticifolia in 3T3-L1 Cells
- Antioxidant Activity of Hydroxyflavonoids
- Antiproliferative Effects Associated with Membrane Lipid Interaction of Green Tea Catechins
- Cell Growth Inhibition by Membrane-Active Components in Brownish Scale of Onion
- Growth Inhibition of Stilbenoids in Welwitschiaceae and Gnetaceae through Induction of Apoptosis in Human Leukemia HL60 Cells(Molecular and Cell Biology)
- Stilbenoids with One Epoxy Group from Cotylelobium lanceolatum
- Vaticanol C-Induced Cell Death Is Associated with Inhibition of Pro-Survival Signaling in HL60 Human Leukemia Cell Line
- Stilbenoids from Leaves of Upuna borneensis
- Characterization of the CYP2C8 Active Site by Homology Modeling
- Characterization of the CYP3A4 Active Site by Homology Modeling
- 1,6-Asymmetric Induction by Reductive Acetal Cleavage of a Bicyclic Acetal Using a Sulfinyl Chiral Auxiliary
- 7,7-Dimethyltricyclo[3.3.0.0.^]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7,7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.0^]octan-3-one
- Stereochemistry of the Intramolecular Cyclization Products of Methyl 2-Bromo-5-(4-hydroxyphenyl) hexanoate : Synthesis of trans- and cis-1,4-Dimethyltetralin
- 1,6-Asymmetric Induction Utilizing Asymmetric Desymmetrization by Diastereoselective C-O Bond Fission of the 4-Substituted Bicyclic Acetal : Application to a Synthesis of (-)-Frontalin
- Development of Cellulose Derivatives as Novel Enteric Coating Agents Soluble at pH 3.5-4.5 and Higher
- Cytotoxic Benzophenone Derivatives from Garcinia Species Display a Strong Apoptosis-Inducing Effect against Human Leukemia Cell Lines
- Anti-Platelet and Membrane-Rigidifying Flavonoids in Brownish Scale of Onion
- A New Flavonol Glucoside from Onion
- Inhibitory Effects of Resveratrol Derivatives from Dipterocarpaceae Plants on Tyrosinase Activity(Biochemistry & Molecular Biology)
- Gnetol as a Potent Tyrosinase Inhibitor from Genus Gnetum(Biochemistry & Molecular Biology)
- An Anion Receptor Based on Poly-Substituted Cobalticinium Complexes
- Freezing Bond Rotation by a Pin in Cyclopentadienyl(cyclobutadiene)cobalt(I)Complexes. A New Type of Atropisomerism
- 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. III. : Total Synthesis of (±)-Descarboxyquadrone
- 7,7-Dimethyltricyclo[3.3.0.0^]octan-3-ones as Synthetic Intermediates. II. : A Total Synthesis of (±)-Pentalenene, an Angular Triquinane Sesquiterpene
- A New Resveratrol Hexamer from Upuna borneensis
- Six Flavonostilbenes from Gnetum africanum and Gnetum gnemon
- Asymmetric Synthesis of β-Hydroxy Acid via Stereoselective Dirhodium (II)-Catalyzed C-H Insertion of α-Alkoxydiazoketone
- Four Dimeric Stilbenes in Stem Lianas of Gnetum africanum
- Stilbene Oligomers in Roots of Sophora moorcroftiana
- New phenolic compounds from Camellia sinensis L. leaves fermented with Aspergillus sp.
- New iridoid diesters of glucopyranose from Linaria canadensis (L.) Dum.