- Total synthesis of the fungal metabolite (±)-acremine G: Acceleration of a biomimetic Diels-Alder reaction on silica gel
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A total synthesis of the bioactive tetracyclic natural product acremine G has been achieved in which a regio- and stereoselective biomimetic Diels-Alder reaction between two readily assembled building blocks, accelerated on a solid support (silica gel), forms the key step.
- Mehta, Goverdhan,Khan, Tabrez Babu,Sunil Kumar
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Read Online
- Scalable Wolff-Kishner Reductions in Extreme Process Windows Using a Silicon Carbide Flow Reactor
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A safe and scalable continuous flow strategy for Wolff-Kishner reductions that employs methanol as the solvent has been developed. The use of low-cost hydrazine as the reducing agent in combination with a caustic base provides an atom-efficient, environmentally friendly method for the deoxygenation of aldehydes and ketones to alkanes. Because of the required harsh and corrosive reaction conditions (200 °C, 50 bar), reactor materials such as stainless steel, glass, or any type of polymer have compatibility problems, rendering this process problematic on a production scale. The use of corrosion-resistant silicon carbide (SiC) as the reactor material opens up the possibility of performing Wolff-Kishner reductions on scale with a considerably improved safety profile. Methanol as the solvent significantly simplifies the workup procedure compared with the generally employed high-boiling solvents such as diethylene glycol. The continuous flow protocol was applied to a number of substrates and provided the desired products in good to high yields with space-time yields of up to 152 g L-1 h-1. In addition, a pharmaceutically valuable active pharmaceutical ingredient precursor was synthesized by employing this higherature/pressure Wolff-Kishner protocol.
- Znidar, Desiree,O'Kearney-Mcmullan, Anne,Munday, Rachel,Wiles, Charlotte,Poechlauer, Peter,Schmoelzer, Christoph,Dallinger, Doris,Kappe, C. Oliver
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p. 2445 - 2455
(2019/11/03)
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- Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous-Flow Hydrogenation-Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts
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Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi-Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous-flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous-flow conditions to afford the desired products in good to excellent yields. Especially, air-sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous-flow conditions without decomposition.
- Miyamura, Hiroyuki,Tobita, Fumiya,Suzuki, Aya,Kobayashi, Shū
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supporting information
p. 9220 - 9224
(2019/06/13)
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- Synthesis and antitumor activity evaluation of compounds based on toluquinol
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Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.
- Cheng-Sánchez, Iván,Torres-Vargas, José A.,Martínez-Poveda, Beatriz,Guerrero-Vásquez, Guillermo A.,Medina, Miguel ángel,Sarabia, Francisco,Quesada, Ana R.
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- Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate
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Using a focused microwave reactor, methylation with dimethyl carbonate (DMC) of 1,2- and 1,4-dihydroxybenzene derivatives, found in the product spectrum of lignin depolymerisation, leads to the respective aromatic bis-methyl ethers with excellent isolated yields. Stoichiometric as well as catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective for the bis-methylation of these dihydroxybenzenes at relatively mild temperatures (160-190 °C). Conversion of resorcinol (1,3-dihydroxybenzene) under similar conditions leads to a mixture of 1,3-dimethoxybenzene and methyl 2,4-dimethoxybenzoate. The unusual reactivity of resorcinol's phenyl ring towards DMC can be explained by the synergic effect of its two strongly activating ortho/para directing groups.
- Lui, Matthew Y.,Lokare, Kapil S.,Hemming, Ellen,Stanley, Jessica N.G.,Perosa, Alvise,Selva, Maurizio,Masters, Anthony F.,Maschmeyer, Thomas
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p. 58443 - 58451
(2016/07/06)
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- Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A
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A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).
- Kakde, Badrinath N.,Kumar, Nivesh,Mondal, Pradip Kumar,Bisai, Alakesh
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supporting information
p. 1752 - 1755
(2016/05/19)
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- Charge-transfer complex formations of tetracyanoquinone (cyanil) and aromatic electron donors
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Single-electron oxidants are the primary reagents for investigations of the new oxidants and the development of electron-accepting materials for application in optoelectronics. Quinones are the well-known class of the neutral single-electron oxidants. Here, we present the properties of the strongest neutral electron acceptor of this class tetracyanoquinone (cyanil) and investigate its electron-accepting strength by analyzing the charge-transfer complex formations with the aromatic donor molecules. Charge-transfer complexes of tetracyanoquinone with aromatic electron donors are characterized spectroscopically in solution and isolated as the single crystals.
- Jalilov, Almaz S.,Lu, Jianjiang,Kochi, Jay K.
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- Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation
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Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.
- Tran, Phuong Hoang,Hansen, Poul Erik,Nguyen, Hai Truong,Le, Thach Ngoc
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p. 612 - 618
(2015/02/19)
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- ALKYLATION OF PHENOLIC COMPOUNDS
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The invention relates to a process for O-alkyiation of a phenolic compound comprising at least two hydroxyl groups bonded to an aromatic hydrocarbon, the process comprising reacting the phenolic compound with an alkylating agent in the presence of a base, at a suitable reaction temperature and for a suitable time period, thereby alkylating the at least two hydroxy] groups. The invention also relates to O-alkylaled phenolic compounds produced by this process.
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Page/Page column 36
(2015/04/28)
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- A highly efficient approach to vanillin starting from 4-cresol
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A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.
- Jiang, Jian-An,Chen, Cheng,Guo, Ying,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
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supporting information
p. 2807 - 2814
(2014/05/06)
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- Correlating lignin structural features to phase partitioning behavior in a novel aqueous fractionation of softwood Kraft black liquor
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In this work, a set of softwood lignins were recovered from a Kraft black liquor using a novel pH-based fractionation process involving sequential CO 2 acidification and separation of the solvated aqueous lignin fraction. These recovered lignin fractions were characterized with respect to properties that may be responsible for their phase partitioning behavior as well as properties that may render the lignins more suitable for materials applications. Lignin fractions were recovered between a pH range of 12.8 and 9.5 with the bulk of the lignin (90%) recovered between a pH of 11.1 and 10.0. While all the fractions were found to consist primarily of lignin as validated by sample methoxyl content, the first fractions to phase separated were found to be especially enriched in aliphatic extractives and polysaccharides. From the bulk of the lignin that was recovered between a pH of 11.1 and 10.0 a number of noteworthy trends were discernible from the data. Specifically, the phenolic hydroxyl content was found to exhibit a strong negative correlation to the fractionation pH and exhibited a nearly 50% increase with recovery at decreasing pH, while the GPC-estimated molecular weights and 13C NMR-estimated β-O-4 content showed strong positive correlations to the pH at recovery. The aliphatic hydroxyl content exhibited minimal differences between recovery conditions. Overall, these results suggest that this fractionation approach can generate lignin fractions enriched in select physical or structural properties that may be important for their application as feedstocks for renewable chemicals or materials.
- Stoklosa, Ryan J.,Velez, Julian,Kelkar, Shantanu,Saffron, Christopher M.,Thies, Mark C.,Hodge, David B.
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supporting information
p. 2904 - 2912
(2013/10/08)
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- A convenient and practical synthesis of anisoles and deuterated anisoles by palladium-catalyzed coupling reactions of aryl bromides and chlorides
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Synthesis of anisole: Aryl and heteroaryl halides undergo selective C-O cross-coupling reactions with methanol in the presence of a Pd(OAc) 2/L3 catalyst system. The corresponding ethers were obtained under mild conditions in good yields. The catalytic methodology was also used for the synthesis of labeled deuterated anisoles in good yields (see scheme). Copyright
- Gowrisankar, Saravanan,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 2498 - 2502
(2012/03/27)
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- Diiron complexes with pendant phenol group(s) as mimics of the diiron subunit of [FeFe]-hydrogenase: Synthesis, characterisation, and electrochemical investigation
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Four diiron hexacarbonyl complexes, [Fe2(μ-SCH 2-o-C6H4OMe)2(CO)6] (4a), [Fe2{μ-SCH2-o,m-C6H3(OMe) 2}2-(CO)6] (4b), [Fe2{μ-SCH 2-o,o′-C6H3(CO2Me)(OMe)} 2(CO)6] (4c) and the demethylated form of complex 4a, [Fe2(μ-SCH2-o-C6H4OH) 2(CO)6] (5a), were synthesised and fully characterised. Complexes 4b and 4c were also structurally analysed. Electrochemical investigations revealed that the integrity of the bridging linkages of the examined diiron complexes significantly affect their reduction reversibility and catalysis through a coupled chemical reaction in a unique ECE mechanism, widely adopted by complexes with the core {Fe2(CO)4-6}. Demethylation of complexes 4a and 1Me, [Fe2(μ-SCH 2)2CMe(CH2-o-C6H4OMe)(CO) 6], by BBr3 led to complexes (5a and 1H, [Fe 2(μ-SCH2)2CMe(CH2-o-C 6H4OH)-(CO)6]) with pendant phenol group(s), a weak acid. Deprotonation of the two complexes produced the pendant phenolate, which instantly intramolecularly substitutes the bound CO to yield species of the coordination form FeI-OR (R = phenolic moiety). Electrochemical investigation revealed that the pendant phenol groups in complexes 1H and 5a do not seem to improve their catalytic efficiency in proton reduction in the medium acetic acid/dichloromethane.
- Tang, Ying,Wei, Zhenhong,Zhong, Wei,Liu, Xiaoming
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experimental part
p. 1112 - 1120
(2011/06/10)
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- Synthesis and structural revision of (±)-laurentristich-4-ol
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(Chemical Equation Presented) The structure of tetracyclic natural sesquiterpene laurentristich-4-ol was revised based on its synthetic studies. The proposed and the revised structures of laurentristich-4-ol were both synthesized with SmI2-mediated ketyl radical cyclization as the key step to construct the spirocyclic ether skeleton.
- Chen, Pinhong,Wang, Junhua,Liu, Kun,Li, Chaozhong
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p. 339 - 341
(2008/09/17)
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- Synthesis of triprenylated toluquinone and toluhydroquinone metabolites from a marine-derived Penicillium fungus
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Two triprenylated toluquinone and toluhydroquinone marine fungal metabolites, 5-methyl-2-[(2′E,6′E)-3′,7′,11′-trimethyl-2′,6′,10′-dodecatrienyl]-2,5-cyclohexadiene-1,4-dione and 5-methyl-2-[(2′E,6′E)-3,7,11-trimethyl-2′,6′,10′-dodecatrienyl]-1,4-benzenediol, were synthesized in four and five steps, respectively, from 2-methyl-1,4-benzoquinone. The synthesis extends the applicability of the oxidative ether cleavage of hydroquinone dimethyl ethers with argentic oxide under acidic conditions to include the oxidative demethylation of polyprenylated-1,4-dimethoxy-toluhydroquinones with a quantitative survival of the oxidation- and acid-sensitive polyprenyl side chain.
- Scheepers, Brent A.,Klein, Rosalyn,Davies-Coleman, Michael T.
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p. 8243 - 8246
(2007/10/03)
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- Friedel-Crafts Benzylation of 1,4-Dialkoxybenzenes - Cleavage and Rearrangement of Esters and Methoxymethyl Ethers in ZnCl2 Montmorillonite K10 Clay
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Benzylation of p-dialkoxybenzenes can be achieved through the use of modified montmorillonite K10 clay. For the first time, synthese of nitro-diarylmethanes were obtained by Friedel-Crafts alkylation with good yields. In the case of p-methoxymethyl phenyl ether and phenyl ester, selectivity favoring Fries rearrangement over benzylation is reported.
- Waterlot, C.,Couturier, D.,Hasiak, B.
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p. 417 - 429
(2007/10/03)
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- Baker's yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (-)-curcuquinone and (+)-curcuhydroquinone
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Fermenting baker's yeast converts the unsaturated aldehydes 5a-c into the saturated alcohols 6a-c, respectively. The microbial saturation of substrates adsorbed on a nonpolar resin proceeds in high chemical yields and shows complete enantioselectivity in the formation of the (S)-(+) isomers. Enantiopure 6a-c are versatile chiral building blocks for the synthesis of bisabolane sesquiterpenes. Their usefulness is shown in the preparation of (S)-(+)-curcuphenol, (S)-(+)-xanthorrhizol, (S)-(-)-curcuquinone and (S)-(+)-curcuhydroquinone. The Royal Society of Chemistry 2000.
- Fuganti, Claudio,Serra, Stefano
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p. 3758 - 3764
(2007/10/03)
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- Synthesis and electrochemistry of platinum complexes of hydroquinon-2-ylmethyl- and p-benzoquinon-2-ylmethyldiphenylphosphine
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Platinum(II) complexes of new (hydroquinon-2-ylmethyl)diphenylphosphine (PPh2thqH2) and diphenyl(quinon-2-ylmethyl)phosphine (PPh2tq) ligands have been studied. Reaction of (2,5-dimethoxybenzyl)diphenylphosphine (PPh2dmb) with [PtCl2(PhCN)2] afforded [PtCl2(PPh2dmb)2] 1a. Metathesis reactions gave the bromo (1b) and iodo (1c) congeners. Deprotection of the hydroquinone groups in 1a using boron tribromide followed by treatment with base produced the O,P-chelated hydroquinonate phosphine complex, cis-[Pt(O,P-PPh2thqH)2] 2. Reaction of 2 with hydrobromic acid afforded cis-[PtBr2(PPh2thqH)2] 3 which can be oxidised to give the quinone phosphine complex cis-[PtBr2(PPh2tq)2] 4. Unlike previously reported quinone phosphine complexes, 4 is robust and stable to hydrolysis; its reduction with excess of zinc and dilute hydrobromic acid produced cis-[Pt(O,P-PPh2thqH)2(ZnBr2)] 5. Crystal structure analyses of 2·2dmf, 4·0.5dcm and 5·2dmf were performed. The electrochemistries of 1b, 3, and 4 have been characterised by cyclic voltammetry and controlled potential electrolyses. Cyclic voltammograms of 4 in the presence of dilute hydrobromic acid exhibit a four-electron cathodic process, attributed to reduction to 3; those of 3 show an anodic process attributed to oxidation to 4. The electrochemistry of 4 under aprotic conditions is extraordinary. Although there are two well separated, pendant quinone substituents only a single one-electron reduction process is observed. The reduction affords a radical species (6?-) which has been characterised by cyclic voltammetry, and by EPR and UV/Vis/NIR spectroscopy. It is argued from the available data that 6?- is a novel platinum(IV) complex with bound hydroquinonate and semiquinonate (sq) groups, namely [PtBr2(O,P-PPh2thq)(O,P-PPh2tsq ?)]-, and a possible mechanism for its remarkable formation is discussed.
- Sembiring, Seri Bima,Colbran, Stephen B.,Craig, Donald C.
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p. 1543 - 1554
(2007/10/03)
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- Addition of organolithium reagents to some carbohydrate enones
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Addition of organolithium reagents to die sugar enones: alkyl 2,3,6-trideoxy-α-L- and 2,3-dideoxy-α- D-hex-2-enopyranosid-4-ulose has been examined. Butyl, benzyl and 2,5-dimethoxy-4-methylphenyllithium add, with increasing stereoselectivity, to the carbonyl group of the α,β-unsaturated ketosugars, whereas 2,5-dimethoxybenzyllithium undergoes stereospecific conjugate addition and 1,2-addition in die ratio of 1.7:1. The structure of the resultant carbinols is based on X-ray crystallographic evidence.
- Achmatowicz, Osman,Szechner, Barbara,Maurin, Jan K.
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p. 6035 - 6044
(2007/10/03)
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- ortho-Directed metallation in the regiocontrolled synthesis of enantiopure 2- and/or 3-substituted (S)S (p-tolylsulfinyl)-1,4-benzoquinones
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Enantiomerically pure (S)S-(p-tolylsulfinyl)-1,4-benzoquinones with alkyl and methoxy substituents at C-2 and/or C-3 are synthesized by CAN oxidation of adequately substituted (S)S-(p-tolylsulfinyl)-1,4-dimethoxyaromatic precursors 2 or 3. These compounds were obtained by ortho-directed metallation or bromo-metal exchange from the corresponding p-methoxyanisoles in a highly regiocontrolled manner.
- Carreno, M. Carmen,Garcia Ruano, Jose L.,Toledo, Miguel A.,Urbano, Antonio
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p. 913 - 921
(2007/10/03)
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- In situ fourier transform infrared spectroscopy of molecular adsorbates at electrode-electrolyte interfaces: A comparison between internal and external reflection modes
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The vibrational properties of 2,5-dihydroxybenzyl mercaptan (DHBM) irreversibly adsorbed on gold electrodes have been examined in situ in aqueous 0.1 M HC1O4 by two different Fourier transform infrared (FT-IR) spectroscopic techniques: (i) potential difference attenuated total reflection FT-IR (PD-ATR-FT-IR), using a thin layer of gold (~4 nm) sputtered on a (thick layer) Au-patterned ZnSe internal reflection element as the electrode and (ii) PD-FT-IR (external) reflection absorption spectroscopy (PD-FT-IRRAS) on a solid Au electrode. The results obtained with both techniques, using the spectrum of the monolayer in the reduced state as a reference, were found to be nearly identical, displaying a set of negative- and positive-pointing features. The first set matched, within experimental error, the most prominent peaks observed in the ATR-FT-IR spectra of the DHBM monolayer using either pure water or 0.1 M HC1O4 as a reference. Furthermore, the positive-pointing features in the PD-FT-IR spectra, which correspond to the product of the electrochemical oxidation of irreversibly adsorbed DHBM, were consistent with the presence of a quinone-type moiety, as would be expected on the basis of chemical considerations. These observations indicate that, to the level of sensitivity of these two methodologies, the mode of adsorption and reactivity of DHBM (and probably a number of other species as well) is not appreciably affected by possible differences in the metal surface microstructure.
- Bae,Sandifer,Lee,Tryk,Sukenik,Scherson
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p. 4508 - 4513
(2007/10/02)
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- Selective nitration versus oxidative dealkylation of hydroquinone ethers with nitrogen dioxide
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Various alkyl-substituted p-dialkoxybenzenes (ArH) react readily with nitrogen dioxide (NO2) in dichloromethane solution via either nitration (ArNO2) or oxidative dealkylation to quinones (Q). Spectral transients indicate that these coupled processes proceed from the dialkoxybenzene radical cation (ArH+) formed as the common reactive intermediate from electron-transfer in the disproportionated precursor [ArH, NO+]NO3-. In fast subsequent steps, ArH+ undergoes homolytic coupling with NO2 (which leads to aromatic nitration) and nucleophilic attack of NO3- (which results in oxidative dealkylation). As such, the competition between nitration and oxidative dealkylation is effectively modulated by solvent polarity and added nitrate.
- Rathore,Bosch,Kochi
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p. 6727 - 6758
(2007/10/02)
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- A VERSATILE SYNTHESIS OF HYDROXY-9,10-ANTHRAQUINONE-2-CARBOXYLIC ACIDS
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Islandicin, a mould metabolite, can be synthesised in a few, robust, high yielding steps.This procedure can be further elaborated to give a variety of hydroxy-9,10-anthraquinone-2-carboxylic acids.
- Smith, Colin W.,Ambler, Samantha J.,Steggles, David J.
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p. 7447 - 7450
(2007/10/02)
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- AN EFFICIENT ROUTE TO 3-CHLOROJUGLONES
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The novel 4-chloro-2,5-dimethoxybenzaldehyde 1 has been prepared and converted in only three steps to 5-acetoxy-7-carboethoxy-3-chloro-1,4-naphthaquinone 4.Subsequent Diels-Alder reaction affords a tetracyclic enol ether 9 in a regiospecific manner.
- Bloomer, James L.,Gazzillo, Joseph A.
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p. 1201 - 1204
(2007/10/02)
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- SUBSTITUTED 7,7',8,8'-TETRACYANOQUINODIMETHANES. I. METHODS OF SYNTHESIS OF SUBSTITUTED 7,7',8,8'-TETRACYANOQUINODIMETHANES
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The synthesis of 2-methyl-, 2,5-dimethyl-, and 2-isopropyl-7,7'-8,8'-tetracyanoquinodimethanes was realized from 2-methyl-, 2,5-dimethyl-, and 2-isopropyl-1,4-cyclohexanediones.These cyclic diketones are obtained with good yields by the Birch reduction of 2-chloromethyl-, 2,5-dichloromethyl-, and 2-isopropyl-1,4-dimethoxybenzenes.
- Russkikh, V. S.,Abashev, G. G.
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p. 742 - 745
(2007/10/02)
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- Synthesis of 4,7-Dimethoxyindoles Bearing Substituents at the C-5 and C-6 Positions and Studies on their Demethylation Products
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Syntheses of some 4,7-dimethoxyindoles bearing methyl, amino or acetamido groups at the C-5 and C-6 positions were investigated.The presence of these substituents made possible the isolation of the corresponding 4,7-dihydroxyindole derivatives obtained by long reflux with aluminium chloride in benzene solution.
- Malesani, Giorgio,Galiano, Fabio,Ferlin, Maria Grazia,Masiero, Sergio
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p. 563 - 569
(2007/10/02)
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