Institut de Chimie Moléculaire et des Matériaux d'Orsay

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Méthodologie, Synthèse et Molécules Thérapeutiques

Publications de l'équipe

2018

Unexpected Dimerization of a Tripeptide Comprising a beta,gamma-Diaminoacid. C. Kouklovsky, V. Alezra, J.-P. Baltaze, J. Wan, E. Miclet, Journal of Peptide Science, 2018

Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors. A. Mambrini, D. Gori, C. Kouklovsky, H. Kim, J.-I. Yoshida, V. Alezra, Eur. J. Org. Chem., 2018

Oxidative Coupling of Enolates by Memory of Chirality: an Original Enantioselective Synthesis of Quaternary alpha-Amino Acid Derivatives. A. Mambrini, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Chemical Communications, 2018, 54, 12742 - 12745

N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study toward the Benzofuroindoline Moiety of Bipleiophylline. N. Denizot, R. Guillot, C. Kouklovsky, G. Vincent, Synthesis, 2018, 50, 4823-4828

Combining Pure Shift And J-Edited Spectroscopies: A Strategy For Extracting Chemical Shifts And Scalar Couplings From Highly Crowded Proton Spectra Of Oligomeric Saccharides. D. Pitoux, Z. Hu, B. Plainchont, D. Merlet, J. Farjon, D. Bonnaffe, N. Giraud, Magnetic Resonance in Chemistry, 2018, 56

Diastereoselective Synthesis of an Advanced Intermediate of Thapsigargin and Other 6,12-Guaianolides Using a RCEYM Strategy. M. Jouanneau, K. R. Bonepally, A. Jeuken, A. Tap, R. Guillot, J. Ardisson, J.-P. Férézou, J. Prunet, Org. Lett., 2018, 20, 2176-2180

Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Total Synthesis of (‐)‐17‐nor‐Excelsinidine. M. Jarret, A. Tap, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Angew. Chem. Int. Ed., 2018, 57, 12294-12298

Dearomative Diallylation of N-Acylindoles Mediated by FeCl3. J. Wu, R. K. Nandi, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett., 2018, 20, 1845-1848

Base mediated fragmentation of bicyclic dihydro-3,6-oxazines: transformation of nitroso Diels-Alder cycloadducts. R. Campagne, F. Schäkel, R. Guillot, V. Alezra, C. Kouklovsky, Org. Lett., 2018, 20, 1884-1887

β,γ-Diamino acids as building blocks for new analogues of Gramicidin S: synthesis and biological activity. Y. Wan, A. Stanovych, D. Gori, S. Zirah, C. Kouklovsky, V. Alezra, Eur. J. Med. Chem., 2018, 149, 122-128.

Divergent Oxidative Couplings between Indoles and 2,3-Dihydroxybenzoic Acid Derivatives for the Biomimetic Synthesis of Voacalgine A and Bipleiophylline. N. Denizot, D. Lachkar, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Synthesis, 2018, 50, 4229-4242

In Situ Generation of Cyclopentadienol Intermediates from 2,4-Dienals. Application to the Synthesis of Spirooxindoles via a Domino Polycyclization. A.-S. Marques, J. Marrot, I. Chataigner, V. Coeffard, G. Vincent, X. Moreau, Org. Lett., 2018, 20, 792-795

Constrained cyclic beta,gamma-diamino acids from glutamic acid: synthesis of both diastereomers and unexpected kinetic resolution. V. Alezra, Y. Wan, N. Auberger, S. Thétiot-Laurent, F. Bouillère, A. Zulauf, J. He, S. Courtiol-Legourd, R. Guillot, C. Kouklovsky, S. Cote Des Combes, C. Pacaud, I. Devillers, Eur. J. Org. Chem., 2018, 329-340

Triflic acid as an efficient Brønsted acid promoter for the Umpolung of N-Ac indoles in hydroarylation reactions. R. K. Nandi, A. Perez-Luna, D. Gori, R. Beaud, R. Guillot, C. Kouklovsky, V. Gandon, G. Vincent, Adv. Synth. Catal., 2018, 360, 161–172

Interfering peptides targeting protein–protein interactions: the next generation of drugs? H. Bruzzoni-Giovanelli, V. Alezra, N. Wolff, C.-Z. Dong, P. Tuffery, A. Rebollo, Drug Discovery Today, 2018, 23, 272-285

2017

A Versatile Electronic Tongue Based on Surface Plasmon Resonance Imaging and Cross-Reactive Sensor Arrays-A Mini-Review. L.-A. Garçon, M. Genua, Y.-J. Hou, R. Calemczuk, T. Livache, M. Billon, C. Le Narvor, D. Bonnaffé, H. Lortat-Jacob, Y. Hou, Sensors, 2017, 17, 1046

Radical-Mediated Dearomatization of Indoles with Sulfinate Reagents for the Synthesis of Fluorinated Spirocyclic Indolines. D. Ryzhakov, M. Jarret, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett, 2017, 19, 6336-6339

Expedient Approach to α,β-Unsaturated δ-Lactones via a Catalytic Asymmetric [2+2] Cycloaddition. C. Kouklovsky, A. Rousseau, M. Buchotte, R. Guillot, G. Vincent, Eur. J. Org. Chem., 2017, 6804-6810

Synthesis of N-Sulfonyl Ynamido-Phosphonates: Valuable Partners for Cycloadditions. V. Perez, A. Fadel, N. Rabasso, Synthesis, 2017, 49, 4035-4044

Frozen Chirality of Tertiary Aromatic Amides :Access to Enantioenriched Tertiary alpha-Amino Acid or Amino Alcohol without Chiral Reagent. T. T. Mai, B. Viswambharan, D. Gori, R. Guillot, J.-V. Naubron, C. Kouklovsky, V. Alezra, Chem. Eur. J., 2017, 23, 5787-5798

Revealing the Electrophilicity of N-Ac Indoles with FeCl3: a mechanistic study. R. Beaud, R. K. Nandi, A. Perez-Luna, R. Guillot, D. Gori, C. Kouklovsky, N. E. Ghermani, V. Gandon, G. Vincent, Chem. Commun., 2017, 53, 5834 - 5837

Evaluation of an NIS-Mediated Oxidative Cyclisation of Phenol-Containing N-Acyltryptamine Precursors towards Phalarine: Synthesis of 4′,5′-Dihydrospiro[indole-3,6′-[1,3]oxazine]s. T. Tomakinian, H. Abou Hamdan, N. Denizot, R. Guillot, J.-P. Baltaze, C. Kouklovsky, G. Vincent, Eur. J. Org. Chem., 2017, 19, 2757–2763

Unified biomimetic assembly of voacalgine A and bipleiophylline via divergent oxidative couplings. D. Lachkar, N. Denizot, G. Bernadat, K. Ahamada, M. A. Beniddir, V. Dumontet, J.-F. Gallard, R. Guillot, K. Leblanc, E. O. N'Nang, V. Turpin, C. Kouklovsky, E. Poupon, L. Evanno, G. Vincent, Nature Chemistry, 2017, 9, 793-798

From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis. P. Adler, A. Fadel, J. Prunet, N. Rabasso, Org. Biomol. Chem., 2017, 15, 387-395

2016

CD4-mimetic sulfopeptide conjugates display sub-nanomolar anti-HIV-1 activity and protect macaques against a SHIV162P3 vaginal challenge. K. K. Arien, F. Baleux, D. Desjardins, F. Porrot, Y.-M. Coic, J. Michiels, K. Bouchemal, D. Bonnaffe, T. Bruel, O. Schwartz, R. Le Grand, G. Vanham, N. Dereuddre-Bosquet, H. Lortat-Jacob, SCIENTIFIC REPORTS, 2016, 6

Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles. A.-S. Marques, V. Coeffard, I. Chataigner, G. Vincent, X. Moreau, Org. Lett., 2016, 18, 5296-5299

Recent Progress in Memory Of Chirality (MOC): An Advanced Chiral Pool. V. Alezra, T. Kawabata, Synthesis, 2016, 48, 2997-3016

Efficient synthesis of both diastereomers of β,γ-diamino acids from phenylalanine and tryptophan. N. Auberger, A. Stanovych, S. Thétiot-Laurent, R. Guillot, C. Kouklovsky, S. Cote Des Combes, C. Pacaud, I. Devillers, V. Alezra, Amino Acids, 2016, 48(9), 2237-2242

Synthesis of 3,3-Spiroindolines via FeCl3-Mediated Cyclization of Aryl- or Alkene-Containing 3-Substituted N-Ac Indoles. R. K. Nandi, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett., 2016, 18, 1716-1719

Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles. T. Tomakinian, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Commun., 2016, 52, 5443-5446

Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3. R. K. Nandi, F. Ratsch, R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Commun., 2016, 52, 5328-5331

Synthesis of 5-Phosphonoisoxazoline N-Oxides by Selective O-Alkylation of Nitronate Anions. V. Perez, N. Rabasso, A. Fadel, Eur. J. Org. Chem., 2016, 320-324

2015

Magnetic field dependence of spatial frequency encoding NMR as probed on an oligosaccharide. D. Pitoux, Z. Hu, B. Plainchont, D. Merlet, J. Farjon, D. Bonnaffe, N. Giraud, MAGNETIC RESONANCE IN CHEMISTRY, 2015, 53, 836-844

Connecting Tyrosine and Tryptophan Units of Diazonamide A and Azonazine by a Diastereodivergent Arylative Dearomatization. N. Denizot, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Eur. J., 2015, 21, 18953-18956

Synthesis of 3-arylated indolines from dearomatization of indoles. N. Denizot, T. Tomakinian, R. Beaud, C. Kouklovsky, G. Vincent, Tetrahedron Lett., 2015, 56, 4413-4429

Investigation of the Synthesis of Benzofuroindolines from N-Hydroxyindoles: An O-Arylation/[3,3]-Sigmatropic Rearrangement Sequence. T. Tomakinian, C. Kouklovsky, G. Vincent, Synlett, 2015, 1269-1275

The quest of an oxidative coupling of phenols and indoles towards benzofuroindolines: a two stage approach. R. Beaud, T. Tomakinian, N. Denizot, A. Pouilhès, C. Kouklovsky, G. Vincent, Synlett, 2015, 432-435

Mild Cleavage of N–O Bond of 3,6-Dihydro-1,2-oxazines by Condensation of Aldehydes in Aqueous Media. G. Galvani, R. Lett, C. Kouklovsky, Synlett, 2015, 26, 1340-1344

Fully Resolved NMR Correlation Spectroscopy. D. Pitoux, B. Plainchont, D. Merlet, Z. Hu, D. Bonnaffe, J. Farjon, N. Giraud, Chemistry - A European Journal, 2015, 21, 9044-9047

Cerium(iv) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones. P. Adler, A. Fadel, N. Rabasso, Chem. Commun., 2015, 51, 3612-3615

2014

Landscapes of taste by a novel electronic tongue for the analysis of complex mixtures. L.-A. Garçon, Y. Hou, M. Genua, A. Buhot, R. Calemczuk, D. Bonnaffé, Y. Hou, T. Livache, Sensor Letters, 2014, 12, 1059-1064

Oxidative degradation of amino acids and aminophosphonic acids by 2,2-bipyridine complexes of Copper(II). J. S. Pap, N. El Bakkali-Tahéri, A. Fadel, S. Goger, D. Bogath, M. Molnar, M. Giorgi, G. Speier, A. J. Simaan, J. Kaizer, Eur. J. Inorg. Chem, 2014, 2829–2838

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG-chitotriomycin. G. Despras, A. Alix, D. Urban, B. Vauzeilles, J.-M. Beau, Angew. Chem. Int. Ed., 2014, 53, 11912-11916

Strategies for the synthesis of α- and β-amino vinylphosphonate. P. Adler, A. Fadel, N. Rabasso, Tetrahedron, 2014, 70, 4437-4456

Cyclopropanation of 1,2-dibromoethylphosphonate: a synthesis of β-aminocyclopropylphosphonic acid and derivatives. N. Rabasso, A. Fadel, Tetrahedron Lett., 2014, 55, 6068-6071

Repairing the Thiol-Ene Coupling Reaction. G. Povie, A.-T. Tran, D. Bonnaffe, J. Habegger, Z. Hu, C. Le Narvor, P. Renaud, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53, 3894-3898

Characterization of Glycosaminoglycan (GAG) Sulfatases from the Human Gut Symbiont Bacteroides thetaiotaomicron Reveals the First GAG-specific Bacterial Endosulfatase. J. E. Ulmer, E. M. Vilen, R. B. Namburi, A. Benjdia, J. Beneteau, A. Malleron, D. Bonnaffe, P.-A. Driguez, K. Descroix, G. Lassalle, C. Le Narvor, C. Sandstrom, D. Spillmann, O. Berteau, JOURNAL OF BIOLOGICAL CHEMISTRY, 2014, 289, 24289-24303

Electronic Tongue Generating Continuous Recognition Patterns for Protein Analysis. Y. Hou, M. Genua, L.-A. Garcon, A. Buhot, R. Calemczuk, D. Bonnaffe, H. Lortat-Jacob, T. Livache, JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2014

SPR imaging based electronic tongue via landscape images for complex mixture analysis. M. Genua, L.-A. Garcon, V. Mounier, H. Wehry, A. Buhot, M. Billon, R. Calemczuk, D. Bonnaffe, Y. Hou, T. Livache, TALANTA, 2014, 130, 49-54

Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β-Hydroxy Quaternary α-Amino Acids. B. Viswambharan, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Org. Lett., 2014, 16, 788-791

Regioselective Hydroarylation Reactions of C3 Electrophilic N-Acetylindoles Activated by FeCl3: An Entry to 3-(Hetero)arylindolines. R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Chem. Eur. J., 2014, 20, 7492-7500

Direct Oxidative Coupling of N-Acetyl Indoles and Phenols for the Synthesis of Benzofuroindolines Related to Phalarine. T. Tomakinian, R. Guillot, C. Kouklovsky, G. Vincent, Angew. Chem. Int. Ed., 2014, 53, 11881-11885

Bioinspired Direct Access to Benzofuroindolines by Oxidative [3 + 2] Annulation of Phenols and Indoles. N. Denizot, A. Pouilhès, M. Cucca, R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Org. Lett., 2014, 16, 5752-5755

β,γ-Diamino acid: an original building block for hybrid α/γ-peptide synthesis with extra hydrogen bond donating group. A. Stanovych, R. Guillot, C. Kouklovsky, E. Miclet, V. Alezra, Amino Acids, 2014, 46, 2753-2757

2013

Selective Reduction of Amino Allenephosphonates: Preparation of α-Amino Vinylphosphonates. P. Adler, F. Gomes, A. Fadel, N. Rabasso, Eur. J. Org. Chem., 2013, 7546-7555

p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification. N. Barroca-Aubry, M. Benchekroun, F. Gomes, D. Bonnaffe, Tetrahedron Lett., 2013, 54, 5118-5121

2012

[2,3]-Sigmatropic Rearrangement of Ynamides: Preparation of α-Amino Allenephosphonates. F. Gomes, A. Fadel, N. Rabasso, J. Org. Chem., 2012, 77, 5439-5444

2011

Synthesis of an Enkephalin Analogue Containing an α,α-Disubstituted Heterocyclic Aminophosphonic Acid. N. Rabasso, A. Fadel, Phosphorus, Sulfur Silicon Relat. Elem., 2011, 186, 1811-1819

Highly Regio- and Stereoselective Nickel-Catalyzed Addition of Dialkyl Phosphites to Ynamides: an Efficient Synthesis of β-Aminovinylphosphonates. A. Fadel, F. Legrand, G. Evano, N. Rabasso, Ad. Synth. Catal., 2011, 353, 263-267

2010