A new synthesis of pyrocin and related compounds.
スポンサーリンク
概要
- 論文の詳細を見る
A new synthesis of pyrocin (<B>1</B>) and related compounds is described. The reaction of 2-benzoyl-4,4-dimethyl-2-buten-4-olide (<B>5b</B>) with 2-methyl-1-propenylmagnesium bromide (<B>6</B>) in the presence of CuCl gave α-benzoylpyrocin (<B>7b</B>) in 90% yield. The product of <B>7b</B> with a specific rotation of +2.43° was obtained when the reaction was carried out in the presence of (−)-sparteine. α-Acetylpyrocin (<B>7a</B>) was prepared in the similar manner in 63% yield. The treatment of <B>7a</B> and that of <B>7b</B> with ethanolic sodium ethoxide gave <B>1</B> in 65% and 81% yields, respectively. The reaction of <B>1</B> with large excess of SOCl<SUB>2</SUB> in absolute ethanol gave ethyl 3-(1-chloro-1-methylethyl)-5-methyl-4-hexenoate (<B>8</B>) in 82% yield. Similar treatment of <B>7</B> with SOCl<SUB>2</SUB> gave ethyl 2-substituted-4-(2-methyl-1-propenyl)-5,5-dimethyl-4,5-dihydrofuran-3-carboxylate (<B>12</B>). Compound <B>8</B> was transformed to ethyl <I>trans</I>-(±)-chrysanthemate (<B>2</B>) in 75% yield.
- 公益社団法人 日本化学会の論文
著者
-
Tsuboi Sadao
Department Of Applied Chemistry Faculty Of Engineering Okayama University
-
Sakai Takashi
Department Of Applied Chemistry Faculty Of Engineering Okayama University
-
Takeda Akira
Department Of Gastroenterology Osaka General Medical Center
-
Shinohara Shohei
Department of Synthetics Chemistry, School of Engineering, Okayama University
関連論文
- Fractionation of metal complexes with dissolved organic matter in a rhizosphere soil solution of a humus-rich Andosol using size exclusion chromatography with inductively coupled plasma-mass spectrometry(Soil Chemistry and Soil Mineralogy)
- Validity and responsiveness of the Oxford hip score in a prospective study with Japanese total hip arthroplasty patients
- Correlation between femoral neck version and strain on the femur after insertion of femoral prosthesis
- Sciatic nerve palsy after cementless total hip arthroplasty. Treatment by modular neck and calcar shortening : a case report
- Femoral anteversion, femoral offset, and abductor lever arm after total hip arthroplasty using a modular femoral neck system
- Optimizing femoral anteversion and offset after total hip arthroplasty, using a modular femoral neck system : an experimental study
- A Case of Vertebral Artery Dissection Associated with Morning Blood Pressure Surge
- Roles of double-balloon endoscopy in the diagnosis and treatment of Crohn's disease : a multicenter experience
- SECRETORY MECHANISM AND PATHOPHYSIOLOGICAL ROLE OF HUMAN ATRIAL NATRIURETIC PEPTIDE IN MEN : Atrial Natriuretic Polypeptide (II) : PROCEEDINGS OF THE 50th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY
- -296- THE DICROTIC NOTCH POSITION ON THE PRESSURE WAVE FORM AT THE BASE OF ASCENDING AORTA : Echo Cardiography : FREE COMMUNICATIONS(II) : PROCEEDINGS OF THE 51th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY
- Fabrication of Superplastic Microtubes Using Dieless Drawing Process
- Crystallographic Orientation Observation and Mechanical Properties Evaluation of Fine-Grained Pure Aluminum
- -0818- THE CLINICAL FEATURES OF UNSTABLE ANGINA EXAMINED BY THE EFFECT OF MEDICAL TREATMENT(PROCEEDINGS OF THE 59th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY)
- -132-THE SECOND COMPONENT OF LEFT VENTRICULAR SYSTOLIC PRESSURE
- Potential Role for Astroglial D-Amino Acid Oxidase in Extracellular D-Serine Metabolism and Cytotoxicity
- Differences in Protein Structure and Similarities in Catalytic Function of Two L-Stereoselective Carbonyl Reductases from Bakers' Yeast
- An Isozyme of Earthworm Serine Proteases Acts on Hydrolysis of Triacylglycerol
- Purification and Characterization of α-Keto Amide Reductase from Saccharomyces cerevisiae
- THE CLINICAL SIGNIFICANSE OF MYOCARDIAL BRIDGING AS A CAUSE OF MYOCARDIAL ISCHEMIA
- IMPROVEMENT IN LONG-TERM PROGNOSIS BY CORONARY BYPASS SURGERY IN PATIENTS WITH 3-VESSEL CORONARY DISEASE : A Matched Case Control Study
- -518-INCIDENCE AND CLINICAL CHARACTERISTICS OF ACUTE PULMONARY EDEMA WITH ACIDOSIS : Heart Failure : FREE COMMUNICATIONS(II) : PROCEEDINGS OF THE 53th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY
- -216- ISCHEMIC EVENTS IN MEDICALLY TREATED SINGLE-VESSEL CORONARY ARTERY DISEASE AND RESTUDY OF CORONARY ANGIOGRAPHY : INDICATION FOR PTCA : PTCA, CABG : FREE COMMUNICATIONS(II) : PROCEEDINGS OF THE 51th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATI
- Compensation Effect between Differential Activation Enthalpy and Entropy in Subtilisin-Catalyzed Kinetic Resolutions of Secondary Alcohols
- Origin of the EnantioselectiYity of Lipases Explained by a Stereo-Sensing Mechanism Operative at the Transition State
- New Optically Active Diporphyrin Having a Chiral Cyclophane as a Spacer
- Highly Efficient and Convenient Regeneration of NADPH for Asymmetric Reduction Using Bakers' Yeast Cell Free Extract
- Effects of Additives in the Reduction Using Bakers' Yeast Cell-Free Extract
- A Convenient Synthesis of Platelet-Activating Factors and Their Analogues from Chiral Epichlorohydrin
- -202-CLINICAL EXPERIENCES OF THE PULSATILE FLOW IN EXTRACORPOREAL CIRCULATION BY USE OF THE PULSATILE ASSIST DEVICE (PAD) : Cardiac Surgery : PROCEEDINGS OF THE 42nd ANNUAL MEETING OF THE JAPANESE CIRCULATION SOCIETY
- Unexpected Course of the Intramolecular Darzens Condensation of Dichloroacetoxybenzaldehyde.A Novel One-step Synthesis of 2, 2-Dichloro-3-(2-hydroxyphenyl)-3-(2-formylphenoxy)propionic Acid
- Blood Pressure, Serum Cholesterol Concentration and Their Related Factors in Urban and Rural Elderly of Ho Chi Minh City
- Loss of Immunostaining of the RBP-Jκ Transcription Factor upon F9 Cell Differentiation Induced by Retinoic Acid^1
- Synthesis of Enantiomerically Pure (R, R)-and (S, S)-1, 2-Bis(pentafluorophenyl)ethane-1, 2-diamine and Evaluation of the pK_a Value by Ab Initio Calculations
- The importance of laminin 5 in the dermal-epidermal basement membrane
- Ifosfamide encephalopathy associated with chemotherapy for musculoskeletal sarcomas : incidence, severity, and risk factors
- THE DETECTION OF INOTROPIC CONTRACTILE RESERVE WITH POSTEXTRASYSTOLIC POTENTIATION IN ACUTELY ISCHEMIC MYOCARDIUM IN THE DOGS : Cardiac Performance : IIIrd Auditorium : Proceedings of the 43rd Annual Meeting of the Japanese Circulation Society, Tokyo, 197
- Basic and clinical studies of percutaneous radiofrequency ablation of osteoid osteoma using a standard electrosurgical generator
- Vulvar basal cell carcinoma with bone metastasis
- PB185 Synthesis of Some Natural Products via the Chiral Reduction of Ketones with Bakers' Yeast
- Practical Resolution of 3-Phenyl-2H-azirine-2-methanol at Very Low Temperature by Using Lipase Immobilized on Porous Ceramic and Optimized Acylating Agent
- Enhancement of the Efficiency of the Low Temperature Method for Kinetic Resolution of Primary Alcohols by Optimizing the Organic Bridges in Porous Ceramic-Immobilized Lipase
- Wound healing in denervated rat skin
- Mixed Duct-Acinar-Islet Cell Tumor of the Pancreas : Report of a Case
- Surgical treatment for chronic lung and thoracic cavity infection
- Transient Behavior of a Saturable Optical Resonator with Distributed Bragg-Reflectors
- Colon Carcinoma After Thymectomy for Myasthenia Gravis : Report of a Case
- Granulocyte-colony-stimulating-factor-producing hepatocellular carcinoma
- Microstructural Investigation of CoNiCrAlY Coated Ni-Based Single Crystal Superalloy Prepared by LPPS
- Extraskeletal myxoid chondrosarcoma with multiple skeletal metastases
- Processing and Functional Evaluation of Titanium Thin Films for Biomimetic Micro Actuator
- Determination of total contents of bromine, iodine and several trace elements in soil by polarizing energy-dispersive X-ray fluorescence spectrometry(Soil Chemistry and Soil Mineralogy)
- Limited Operation for Lung Cancer in Combination with Postoperative Radiation Therapy
- On the riemannian structure all of whose geodesics are closed and of the same length
- Substituent Effects on Redox Potentials of Novel Amphoteric Terphenoquinone Analogues. Unsymmetrically Substituted 2,5-Bis(4-oxo-2,5-cyclohexadien-1-ylidene)-2,5^dihydrothiophenes
- Central Nervous System Relapse of Whipple's Disease
- Surface Micromachining in Optical Isolator with Semiconductor Guiding Layer for Enhancement of Magnetooptic Effect
- The distribution coefficient for cesium in different clay fractions in soils developed from granite and Paleozoic shales in Japan(Soil chemistry and soil mineralogy)
- Warped Products and Riemannian Manifolds Admitting a Function Whose Gradient is of Constant Norm
- First-Principles Study on Electron-Conduction Properties of Single-Row Gold Nanowires
- A highly stereoselective synthesis of (E)-enol lactones by the Wittig reaction of cyclic anhydrides with (.ALPHA.-alkoxycarbonyl-ethylidene)triphenylphosphorane.
- Lagrangian Floer homology of a pair of real forms in Hermitian symmetric spaces of compact type
- Synthesis and 13C NMR spectra of endo-5-(4-imidazolyl)bicyclo[2.2.2]oct-endo- and exo-2-yl trans-cinnamates.
- Asymmetric Reduction of Carbon-Carbon Double Bonds of Conjugated Enones with Fermenting Bakers' Yeast.
- The Reaction of Ethyl Alkylchloropyruvate with Sodiomalonate and Sodioacetoacetate
- Synthesis and hydrolysis of 4-acetoxymethylbenzimidazoles. Effects of freezing an internal rotation on intramolecular catalysis by a benzimidazolyl group.
- A new method for the synthesis of 3,5-disubstituted 2(5H)-furanones. Synthesis of (.+-.)-acarenoic acid.
- Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furans and selenophenes.
- A stereoselective synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid), the sex attractant of the black carpet beetle.
- Electrochemical reduction of exo-5-acetyl-endo-6-trichloromethylbicyclo[2.2.1]hept-2-ene.
- Oxidation of alcohols with electrolytic manganese dioxide. Its application for the synthesis of insect pheromones.
- Asymmetric synthesis of (2R,3S)-2,3-epoxyoctanal, a key intermediate of 14,15-leukotriene A4.
- Chemistry of α-Haloaldehyde. VI. Reaction of 2-Chloro-2-methylpropanal with Benzoylacetonitrile in the Presence of Potassium Carbonate
- A new synthesis of pyrocin and related compounds.
- A new synthesis of 4-methoxy-6-valeryl-5,6-dihydro-2-pyrone.
- Diels-AIder Reactions of 5,5,5-Trichloro-3-penten-2-one and Related Compounds
- Synthesis of methyl-substituted 1-cyclopentene-1-carboxylates and related compounds.
- Reaction of Ethyl α,α-Dichloroacetoacetate with Aldehydes
- Electrolyses of 2,2-Dichloro-3-phenylcyclopropanecarboxylic Acids in Hydroxylic Solvents with a Platinum Anode
- Acute calcific tendinitis of the gluteus medius : a case report with serial magnetic resonance imaging findings
- t-BuCl-NaI as a reagent for the selective reduction of olefinic double bond of .BETA.-phenyl .ALPHA.,.BETA.-unsaturated carbonyl compounds.
- A convenient synthesis of 4-(2,2-dichloroethenyl)-5,5-dimethyl-tetrahydro-2-furanone derivatives, a key intermediate of permethrinic acid.
- A Michael addition-induced Favorskii rearrangement.
- Reinvestigation of base-catalyzed condensation of ethyl .ALPHA.,.ALPHA.-dichloroacetoacetate with aldehydes. A new synthesis of (.+-.)-disparlure.
- Synthesis of 5-[(E)-1-alkenyl]-3(2H)-furanones by the stereoselective dehydration with Me3SiCl.
- Chemistry of α-Haloaldehydes. II. Base-catalyzed Condensation of α-Haloaldehydes with Methyl Chloroacetate
- The Base-catalyzed Condensation of α-Haloaldehydes with Dichloroacetates
- Asymmetric reduction of .ALPHA.-(dimethylthiocarbamoylthio) carbonyl compounds with bakers' yeast.
- Highly enantioselective reduction of ethyl 2-acyloxy-3-oxobutanoate with immobilized Baker's yeast.
- Favorskii-type rearrangement of .ALPHA., .ALPHA.'-dihalo ketones induced by enolates of (diethoxyphosphinyl)acetic esters and its application to the synthesis of .ALPHA., .ALPHA.'-divinyl ketones.
- Favorskii-type rearrangement of .ALPHA.,.ALPHA.'-dihalo ketones with sodiomalonates leading to conjugated enone derivatives.
- One-pot C-arylmethylation of active methylene compounds with aromatic aldehydes induced by a Me3SiCl-NaI-MeCN reagent.