- Neopentyl Esters as Robust Linkers for Introducing Functionality to Bis-MPA Dendrimers
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A series of neopentyl carboxylic acids bearing functionality amenable to click chemistry were prepared and then appended to high-generation bis-MPA dendrons via fluoride-promoted esterification. The nucleophilic stability of neopentyl and non-neopentyl dendrons in acidic to basic phosphate buffers was compared by monitoring degradation via quantitative 1H nuclear magnetic resonance (NMR). The neopentyl periphery dendrons were found to be highly resistant to hydrolysis under all experimental conditions. The neopentyl groups also did not impede click functionalization onto the dendrons.
- Deng, Billy,McNelles, Stuart A.,Da-Ré, Giancarlo,Marando, Victoria M.,Ros, Samantha,St?ver, Harald D. H.,Adronov, Alex
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p. 270 - 275
(2022/01/20)
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- Preparation of cyclic imides from alkene-tethered amides: Application of homogeneous Cu(ii) catalytic systems
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A Cu-based homogeneous catalytic system was proposed for the preparation of imides from alkene-tethered amides. Here, O2 acted as a terminal oxidant and a cheap and easily available oxygen source. The cleavage of CC bonds and the formation of C
- Chen, Suqing,Liu, Zhenghui,Mu, Tiancheng,Ou, Hualin,Tan, Xingxing,Wang, Peng,Yan, Zhenzhong,Yu, Dongkun,Zhao, Xinhui
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p. 7698 - 7707
(2020/03/13)
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- mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives
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A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.
- Deng, Xiaojun,Zhang, Luwen,Liu, Huixia,Bai, Yu,He, Wei
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supporting information
(2020/11/24)
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- Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates for the Synthesis of Sulfonylated Pyrrolidones
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A copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones is described. This reaction features good functional group tolerance and wide substrate scope, providing an efficient and straightforward protocol to access this kind of pyrrolidones. Moreover, preliminary mechanistic investigations disclosed that a free-radical pathway might be invovled in the process.
- Rao, Wei-Hao,Jiang, Li-Li,Liu, Xiao-Meng,Chen, Mei-Jun,Chen, Fang-Yuan,Jiang, Xin,Zhao, Jin-Xiao,Zou, Guo-Dong,Zhou, Yu-Qiang,Tang, Lin
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supporting information
p. 2890 - 2893
(2019/04/30)
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- Iridium-Catalyzed Intramolecular Oxidative Cyclization of Alkenyl Amides and Alkenoic Acids
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An iridium/dppf complex efficiently catalyzed the oxidative cyclization of N sulfonyl alkenyl amides and alkenoic acids. Electron deficiena?t alkenes were effective as sacrificial hydrogen acceptors. High selectivity of the oxidative cyclization over the
- Nagamoto, Midori,Nishimura, Takahiro,Yorimitsu, Hideki
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p. 4272 - 4282
(2017/09/13)
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- Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol
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We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [Acr-Mes]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3-hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ-lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.
- Ramirez, Nieves P.,Gonzalez-Gomez, Jose C.
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supporting information
p. 2154 - 2163
(2017/04/24)
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- An improved new path to synthesize gemfibrozil
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A new route has been developed for synthesis of gemfibrozil in good yield with high purity. The obtained gemfibrozil was characterized by using IR, 1H NMR, 13C NMR and mass spectral studies. According to Biopharmaceutical Classification System, gemfibrozil is classified under class-II drugs (low solubility-high permeability) and an antihyperlipidimic. So it's admirable to synthesize the intention molecule in easy and economical way.
- Nunna, Rambabu,Jayanna,Ramachandran
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p. 925 - 928
(2015/02/05)
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- N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation
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A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
- Osberger, Thomas J.,White, M. Christina
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supporting information
p. 11176 - 11181
(2014/08/18)
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- Isomerizing ethenolysis as an efficient strategy for styrene synthesis
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A shrinking chain: A bimetallic system consisting of [{Pd(μ-Br)(tBu 3P)}2] and a ruthenium metathesis catalyst has been found to efficiently promote the cross-metathesis between substituted alkenes and ethylene, while continuously migrating the double bond along the alkenyl chain (see scheme). When alkenylarenes, such as the natural products eugenol, safrol, or estragol, were treated with this catalyst under an ethylene atmosphere, they were cleanly converted into the corresponding styrenes and propylene gas. Copyright
- Baader, Sabrina,Ohlmann, Dominik M.,Goossen, Lukas J.
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supporting information
p. 9807 - 9810
(2013/08/23)
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- A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: Synthesis of (±)-trachelanthamidine
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Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine (see scheme; TIPS-EBX=triisopropylsilyl ethynylbenziodoxolone).
- Nicolai, Stefano,Piemontesi, Cyril,Waser, Jerome
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supporting information; experimental part
p. 4680 - 4683
(2011/06/23)
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- Metal-free oxyaminations of alkenes using hydroxamic acids
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A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.
- Schmidt, Valerie A.,Alexanian, Erik J.
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supporting information; experimental part
p. 11402 - 11405
(2011/09/16)
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- Total synthesis of natural and non-natural δ 5,6δ12,13-jatrophane diterpenes and their evaluation as MDR modulators
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We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.
- Schnabel, Christoph,Sterz, Katja,Mueller, Henrik,Rehbein, Julia,Wiese, Michael,Hiersemann, Martin
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supporting information; experimental part
p. 512 - 522
(2011/04/22)
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- Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine
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(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.
- Nicolal, Stefano,Erard, Stephane,Gonzalez, Davinla Fernandez,Waser, Jerome
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supporting information; experimental part
p. 384 - 387
(2010/03/04)
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- Metal-free, aerobic dioxygenation of alkenes using hydroxamic acids
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(Chemical equation presented) One dioxygenation please, hold the metal: In the presence of either oxygen or air as the sole oxidant and external oxygen atom source, a variety of unsaturated hydroxamic acids afford cyclic hydroxamates that are readily converted into 1,2-diols, with the potential for high levels of reaction stereocontrol.
- Schmidt, Valerie A.,Alexanian, Erik J.
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supporting information; scheme or table
p. 4491 - 4494
(2010/08/21)
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- Platinum-catalyzed intramolecular hydrohydrazination: Evidence for alkene insertion into a Pt-n bond
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Dicationic (bpy)Pt(II) complexes were found to catalyze the intramolecular hydrohydrazination of alkenes. Reaction optimization revealed Pt(bpy)Cl 2 (10 mol %) and AgOTf (20 mol %) in DMF-d7 to be an effective catalyst system for the conversion of substituted hydrazides to five- and six-membered N-amino lactams (N-amino = N-acetamido at 120 A°C, N-phthalimido at 80 A°C, -OTf = trifluoromethanesulfonate). Of the four possible regioisomeric products, only the product of 5-exo cyclization at the proximal nitrogen is formed, without reaction at the distal nitrogen or 6-endo cyclization. The resting states were found to be a 2:1 Pt-amidate complex (25, for N-acetamido) of the deprotonated hydrazide and a Pt-alkyl complex of the cyclized pyrrolidinone (20 for N-phthalimido). Both complexes are catalytically competent. Catalysis using 25 as the precatalyst shows no rate dependence on added acid (HOTf) or base (2,6-lutidine). The available mechanistic data are all consistent with a mechanism involving N-H activation of the hydrazide, followed by insertion of the alkene into the Pt-N bond, and finally protonation of the resulting cyclized alkyl complex by hydrazide to release the hydrohydrazination product and regenerate the active Pt-amidate catalyst.
- Hoover, Jessica M.,Dipasquale, Antonio,Mayer, James M.,Michael, Forrest E.
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body text
p. 5043 - 5053
(2010/06/13)
-
- Acyloxylactonisations mediated by lead tetracarboxylates
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The reaction of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains has been found to give acyloxy lactone products in a diastereoselective process; the reaction can be extended to lead(IV) tetrazolates to give the analogous outcome. Mechanistic implications of these results are discussed.
- Cottrell, Ian F.,Cowley, Andrew R.,Croft, Laura J.,Hymns, Lauren,Moloney, Mark G.,Nettleton, Ewan J.,Kirsty Smithies,Thompson, Amber L.
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supporting information; experimental part
p. 2537 - 2550
(2009/08/07)
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- Processes of making gamma,delta-unsaturated carboxylic acid and silyl ester thereof, carboxyl group-containing organosilicon compound and process of making
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A γ,δ-unsaturated carboxylic acid silyl ester is prepared by reacting an α,β-unsaturated carboxylic acid ester with a hydrosilane or hydrosiloxane in the presence of tris(pentafluorophenyl)borane. γ,δ-Unsaturated carboxylic acid derivatives are readily prepared through fewer steps and in high yields.
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Page/Page column 9
(2010/02/11)
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- Transition-metal catalyzed synthesis of δ-hydroxy-γ-lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via γ-unsaturated carboxylic acids. Comments on the formation of α-cyclopropyl carboxylic acids
-
Bis(trimethylsilyl)ketene acetals react with allylic acetates in the presence of Pd(0) complexes to give γ-unsaturated carboxylic acids together with α-cyclopropyl carboxylic acids. The unsaturated acids can be converted catalytically to δ-hydroxy-yγ-lactones by the H2O2/MTO system (methyltrioxorhenium) and to butenolides by Pd(II) catalyzed intramolecular cyclization reactions. The structure of two of these lactones has been established by X-ray analysis. The mechanism of the formation of the cyclopropanic acids will be discussed.
- Rudler, Henri,Harris, Paul,Parlier, Andrée,Cantagrel, Frédéric,Denise, Bernard,Bellassoued, Moncef,Vaissermann, Jacqueline
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p. 186 - 202
(2007/10/03)
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- Intramolecular functionalisation by a methylene radical of a 1,2-diol and a vicinal amino alcohol: Models for coenzyme B12-dependent diol dehydratase and ethanolamine ammonia lyase
-
Coenzyme B12-dependent diol dehydratase converts 1,2-diols (e.g. propane-1,2-diol) into the corresponding aldehyde and water. The similar enzyme ethanolamine ammonia lyase transforms vicinal aminoalcohols (e.g. 2-aminoethanol) into the corresponding aldehyde and ammonia. Model systems have been developed that replicate key features of the putative enzymatic mechanism, i.e. removal of a hydrogen atom from the CH2OH group of a 1,2-diol or vicinal aminoalcohol by a methylene radical derived from an alkylcobalt compound, and conversion of a 1,2-diol or vicinal aminoalcohol into a carbonyl compound and water or ammonia triggered by such a methylene radical. The models are based on alkyl(pyridine)bis(dimethylglyoximato)cobalt complexes [alkyl(pyridine)cobaloximes, Cbx], which were synthesised from appropriate organic precursors using standard methodology. The complexes contain a 1,2-diol [as in 4,5-dihydroxy-2,2-dimethylpentyl(pyridine)cobaloxime] or vicinal aminoalcohol [as in 6-amino-5-hydroxy-2,2-dimethylhexyl(pyridine)cobaloxime] tethered to the cobalt by a carbon chain. Photolysis or thermolysis of 4,5-dihydroxy-2,2-dimethylpentyl(pyridine)cobaloxime at pH 3 or 9 gave 4,4-dimethylpentanal. It is proposed that homolysis of the Co-C bond of 4,5-dihydroxy-2,2-dimethylpentyl(pyridine)cobaloxime induced by photolysis or thermolysis affords the 1,2-dihydroxy-4,4-dimethyl-l-pentyl radical via a 1,5-H shift, which is converted into the 4,4-dimethyl-1-oxo-2-pentyl radical, and hence 4,4-dimethylpentanal. The pathway for formation of the aldehyde was diagnosed using the specifically deuteriated analogue [5,5-2H 2]-4,5-dihydroxy-2,2-dimethylpentyl(pyridine)-cobaloxime, which gave [1,5-2H2]-4,4-dimethylpentanal accompanied by 3,3-dimethylbutanal on thermolysis or photolysis at pH 3. The protected model compound 2a was hydrolysed to 6-amino-5-hydroxy-2,2-dimethylhexyl(pyridine)cobaloxime, which was heated at pH 3 or 9 to give 5,5-dimethylhexan-2-one and ammonia. The Royal Society of Chemistry 2000.
- Andersen, Rosaleen J.,Ashwell, Susan,Garnett, Ian,Golding, Bernard T.
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p. 4488 - 4498
(2007/10/03)
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- Pinacol-type rearrangements of intramolecular photocycloadducts: Application of the 2,2-dimethyl-4-pentenoate protecting group
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A pinacol-type rearrangement of intramolecular photocycloadducts has been accomplished by exploiting a novel ester protecting group that can be easilyremoved from a hindered alcohol. The ester is removed by an intramolecular lactonization, overcoming the steric factors normally associated with pivalate esters.
- Crimmins, Michael T.,Carroll, Charlotte A.,Wells, Angela J.
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p. 7005 - 7008
(2007/10/03)
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- Intermolecular free radical reactions on solid support. Allylation of esters
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The first examples of intermolecular free radical allylation reactions on solid support are reported. The allylation proceeds in good chemical efficiency with a variety of substrates as well as allylating agents. Control experiments indicate that the polymer matrix is inert to the reaction conditions.
- Sibi, Mukund P.,Chandramouli, Sithamalli V.
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p. 8929 - 8932
(2007/10/03)
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- A Facile Method for Synthesis of Three Carbon-Homologated Carboxylic Acid by Regioselective Ring-opening of β-Propiolactones with Organocopper Reagents
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Organocopper reagents, such as diorganocuprates, organocopper-tributylphosphine, and Grignard reagents in the presence of a copper (I) salt, reacted with β-propiolactones by regioselective β-carbon-oxygen fission to give 3-substituted propionic acids.Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening of sterically hindered β-propiolactones such as β-methyl- and α,β-dimethyl-β-propiolactones and also in the reactions using the organocopper reagents with vinyl and allyl substituents.The ring-opening of β-propiolactone was confirmed to proceed by SN2 pathway with predominant inversion of configuration of the β-carbon by using the reaction of cis-α,β-dimethyl-β-propiolactone with di-tert-butylcuprate to afford syn-2,3,4,4-tetramethylpentanoic acid.
- Kawashima, Masatoshi,Sato, Toshio,Fujisawa, Tamotsu
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p. 403 - 412
(2007/10/02)
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- An E.S.R. Investigation of Ethoxy and Trimethylsilyloxy Iminyl Radicals
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Trimethylsilyloxy and ethoxy iminyls (4a-i) have been generated by photolysis of solutions of the corresponding trimethylsilyl and ethyl N-chloro imidates, in the cavity of an e.s.r. spectrometer.The unpaired electron resides in a 2py orbital o
- Glover, Stephen A.,Beckwith, Athelstan L. J.
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p. 701 - 709
(2007/10/02)
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- INTRAMOLECULAR HOMOLYTIC DISPLACEMENTS 7 - FREE RADICAL ADDITIONS TO UNSATURATED PEROXY COMPOUNDS : SYNTHESIS OF OXYGENATED HETEROCYCLES
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Free radical additions of hydrogen donor solvents to tert-butyl perpent-4-enoate have given 4-substituted γ-butyrolactones, with yields of 50 percent or greater.Such reactions applied to allyl-tert-butyl peroxide have produced 2,3-epoxypropanation of these solvents.Similar addition-elimination processes occurred with tert-butyl 4-methyl-perpent-4-enoate, tert-butyl 2,2-dimethyl-perpent-4-enoate and tert-butyl-methallyl peroxide, but they failed with tert-butyl 5-methyl-perhex-4-enoate and tert-butyl-3-methyl-but-2-enyl peroxide.
- Maillard, Bernard,Kharrat, Abdelmajid,Rakotomanana, Felicien,Montaudon, Evelyne,Gardrat, Christian
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p. 4047 - 4056
(2007/10/02)
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- Synthesis of 4-Penten-4-olides (γ-Methylene-γ-butyrolactones) via 4-Pentenoic Acids
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4-Penten-4-olides (γ-Methylene-γ-butyrolactones) 7 are easily accessible starting from allylic alcohols 1, which on ortho ester Claisen rearrangement and hydrolytic work-up furnish 4-pentenoic acids 5.The latter on iodolactonization and hydrogen iodide elimination by means of 1,8-diazabicycloundec-7-ene (DBU) furnish 7, in good over-all yield and with variable substitution patterns. - Iodolactonization under kinetic control shows moderate 1,2- or 1,3-asymmetric induction (3:1 and ca. 2:1, respectively).The composition of the iodolactone mixtures 6 as well as the individual relative configurations are deduced from 1H and 13C NMR data. - Similary, the spirobipentenolide 13 is obtained starting from diethyl diallylmalonate (9) via 11 resulting from ester iodocyclization.
- Guenther, Hans Juergen,Guntrum, Eberhard,Jaeger, Volker
-
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- Effects of α-Substitution on the Rate of Chloromercuriolactonization of Phenyl Esters of γδ-Unsaturated Acids
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Second-order rate constants for the reaction of several phenyl esters of α-alkyl- and/or α-aryl-substituted allyacetic acids with mercury(II) chloride have been determined in 50percent aqueous ethanol.It was found that α-substitution increases the rate of reaction.The rate constants can be correlated with the dual substituent parameter expressions (i) and (ii).In the systems studied the steric coefficient is much larger than the polar one, suggesting that the effect of the substituents on the rate of the reaction is essentially steric in nature, with a small additional contribution from the polar effect. log k2 = log k2o + ρ*?* + δEs (i). log k2 = log k2o + ρ*?* + ψν (ii)
- de Almeida, Maria I.,do Amaral, Antonia T.,do Amaral, Luciano
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p. 1953 - 1958
(2007/10/02)
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- Effects of α Substitution on the Carbonyl Stretching Frequencies of Phenyl Carboxylates
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The infrared carbonyl stretching frequencies for several esters of the general formula R1R2R3C-COOPh were determined in carbon tetrachloride.The ?* and Es Taft parameters as well as the νCharton parameters for the same esters were determined.The carbonyl stretching frequencies are well correlated by a dual substituent parameter treatment: νC=O = νC=O0 + ρ*?* + δES or νC=O = νC=O0 + ρ*?* + ΨνCharton.In both cases the steric parameter is much larger than the polar parameter, suggesting that the effect of the substituents on the carbonyl stretching frequencies is of a steric nature, although a small contribution of the polar effect is observed.
- Almeida, Maria Ines de,Amaral, Antonia T. do,Amaral, Luciano do
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p. 1567 - 1571
(2007/10/02)
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- Nucleophilic substitution of 5,5-dimethyl-2-cyclopentenyl derivatives. Lack of SN2' reaction
-
Treatment of tetramethyl-1,3-cyclobutadienone with two equivalents of allyl oxide anion at 140 deg C yields 2,2-dimethyl-4-pentenoic acid which is cyclized via the acid chloride whith aluminium chloride to 5,5-dimethyl-2-cyclopentenone 4.Reduction of 4 with aluminium hydride provides 5,5-dimethyl-2-cyclopentenol 1-OH which is pyrolyzed to 5,5-dimethyl-1,3-cyclopentadiene in dimethylsulfoxide.Reduction of 4 with tri-t-butoxyaluminium hydride at -70 deg C gives 2,2-dimethylcyclopentanone.The 2,6-dichlorobenzoate ester of 1-OH failed to yield SN2' products under a variety of conditions.The rate constants for solvolysis of the p-nitrobenzoate esters of 1-OH, 2-cyclopentenol and Z-2-methyl-4-hexene-3-ol in 80 percent ethanol at 80 deg C are 20.2, 523, and 0.63 x 1E-6s-1, respectively, and the main products of solvolysis are 5-ethoxy-3,3-dimethylcyclopentene, 3-ethoxycyclopentene, and E-2-ethoxy-5-methyl-3-hexene, respectively.There is steric hindrance to solvatation during ionization of the p-nitrobenzoate of 1-OH.
- Kopecky, Karl R.,Levine, Cyril
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p. 3273 - 3279
(2007/10/02)
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- A THREE CARBON HOMOLOGATION BY THE RING-OPENING OF β-PROPIOLACTONES WITH DIORGANOCUPRATES
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Various organocuprates react with β-propiolactones to give β-substituted propionic acids in high yields.
- Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Kawashima, Masatoshi
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p. 2181 - 2184
(2007/10/02)
-