Asymmetric synthesis of (2R,3S)-2,3-epoxyoctanal, a key intermediate of 14,15-leukotriene A4.
スポンサーリンク
概要
- 論文の詳細を見る
Asymmetric reduction of ethyl 3-chloro-2-oxooctanoate with baker's yeast gave ethyl 3-chloro-2-hydroxyoctanoate (<B>3</B>) [(2<I>S</I>,3<I>R</I>)/(2<I>S</I>,3<I>S</I>), 4:1] in 67% yield with >99% e.e. Chlorohydrin (2<I>S</I>,3<I>R</I>)-<B>3</B> was converted to the titled compound in 34% total yield with 80% e.e. via the reduction, dehydrochlorination, and oxidation, successively. (2<I>R</I>,3<I>R</I>)2,3-Epoxyoctanal was also prepared from (2<I>S</I>,3<I>S</I>)-<B>3</B> in 33% total yield with 94% e.e.
- 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
-
Takeda Akira
Department Of Gastroenterology Osaka General Medical Center
-
Furutani Hiroyuki
Department Of Synthetic Chemistry School Of Engineering Okayama University
-
Takeda Akira
Department of Applied Chemistry, Faculty 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)
- 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
- 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
- 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
- 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
- The importance of laminin 5 in the dermal-epidermal basement membrane
- Ifosfamide encephalopathy associated with chemotherapy for musculoskeletal sarcomas : incidence, severity, and risk factors
- Basic and clinical studies of percutaneous radiofrequency ablation of osteoid osteoma using a standard electrosurgical generator
- PB185 Synthesis of Some Natural Products via the Chiral Reduction of Ketones with Bakers' Yeast
- Wound healing in denervated rat skin
- Mixed Duct-Acinar-Islet Cell Tumor of the Pancreas : Report of a Case
- Colon Carcinoma After Thymectomy for Myasthenia Gravis : Report of a Case
- Granulocyte-colony-stimulating-factor-producing hepatocellular carcinoma
- Extraskeletal myxoid chondrosarcoma with multiple skeletal metastases
- 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)
- The distribution coefficient for cesium in different clay fractions in soils developed from granite and Paleozoic shales in Japan(Soil chemistry and soil mineralogy)
- A highly stereoselective synthesis of (E)-enol lactones by the Wittig reaction of cyclic anhydrides with (.ALPHA.-alkoxycarbonyl-ethylidene)triphenylphosphorane.
- 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.
- O07-1 Effects of heated seats in vehicles on thermal comfort and skin temperature
- 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
- 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.
- A novel cell-adhesive scaffold material for delivering keratinocytes reduces granulation tissue in dermal wounds
- Evaluation of efficacy and safety of finasteride 1 mg in 3177 Japanese men with androgenetic alopecia