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Your search keyword '"Vincent Servajean"' showing total 6 results
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6 results on '"Vincent Servajean"'

1. Total Synthesis of Tiacumicin B: Implementing Hydrogen Bond Directed Acceptor Delivery for Highly Selective β‐Glycosylations

Author

Cédric Tresse, Guillaume Masson, Grégory Genta-Jouve, Jean-Marie Beau, Emmanuel Roulland, Louis Jeanne-Julien, Vincent Servajean, Stéphanie Norsikian, Marc François-Eude, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie moléculaire (LCM), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de neurosciences cognitives de la méditerranée - UMR 6193 (INCM), Université de la Méditerranée - Aix-Marseille 2-Centre National de la Recherche Scientifique (CNRS), Cibles Thérapeutiques et conception de médicaments (CiTCoM - UMR 8038), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP)

Subjects
Glycosylation, Anomer, Stereochemistry, 010402 general chemistry, 01 natural sciences, Catalysis, chemistry.chemical_compound, Lactones, Coordination Complexes, ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Hydrogen bond, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Enantioselective synthesis, Total synthesis, Hydrogen Bonding, General Medicine, General Chemistry, Acceptor, 0104 chemical sciences, Anti-Bacterial Agents, Aglycone, chemistry, Fidaxomicin
Abstract

International audience; We report a total synthesis of tiacumicin B, a natural macrolide whose remarkable antibiotic properties are used to treat severe intestinal infections. The strategy is in part based on our experience of the synthesis of the tiacumicin B aglycone, and on the decisive use of sulfoxides as anomeric leaving-groups in H-bond-mediated Aglycone Delivery (HAD). This new HAD variant permitted highly b-selective rhamnosylation and noviosylation. To increase convergence, the rhamnosylated C1-C3 fragment thus obtained was anchored to the C4-C19 aglycone fragment by adapting the reliable Suzuki-Miyaura cross-coupling used for the aglycone synthesis. Ring-size selective macrolactonization provided a compound engaged directly in the noviolysation step with a virtually total b-selectivity. The final efficient removal of all the protective groups (PGs) provided synthetic tiacumicin B.

Published
2020
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2. Synthesis of a Tiacumicin B Protected Aglycone

Author

Grégory Genta-Jouve, Jean-Marie Beau, Louis Jeanne-Julien, Guillaume S. Masson, Stéphanie Norsikian, Eloi Astier, Vincent Servajean, and Emmanuel Roulland

Subjects
Glycosylation, Stereochemistry, medicine.drug_class, Antibiotics, Context (language use), 010402 general chemistry, 01 natural sciences, Biochemistry, Catalysis, chemistry.chemical_compound, medicine, Physical and Theoretical Chemistry, Molecular Structure, biology, 010405 organic chemistry, Organic Chemistry, Tiacumicin B, biology.organism_classification, Anti-Bacterial Agents, 0104 chemical sciences, Aglycone, chemistry, Drug Design, Copper, Fidaxomicin, Palladium, Bacteria
Abstract

Tiacumicin B is an antibiotic endowed with the remarkable ability to interact with a new biological target, giving it an inestimable potential in the context of the ever-growing and worrisome appearance of resistances of bacteria and mycobacteria to antibiotics. The synthesis of an aglycone of tiacumicin B ready for glycosylation is reported. The key steps of this approach are a [2,3]-Wittig rearrangement, a Pd/Cu-catalyzed allene-alkyne cross-coupling, a E-selective cross-metathesis, and a final ring-size selective macrolactonization.

Published
2017
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3. Study of the Construction of the Tiacumicin B Aglycone

Author

Stéphanie Norsikian, Grégory Genta-Jouve, Jean-Marie Beau, Louis Jeanne-Julien, Emmanuel Roulland, Vincent Servajean, Eloi Astier, Guillaume Masson, Cibles Thérapeutiques et conception de médicaments (CiTCoM - UMR 8038), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Neurosciences de la Timone (INT), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
010405 organic chemistry, Chemistry, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Total synthesis, Tiacumicin B, Context (language use), 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Aglycone, ComputingMilieux_MISCELLANEOUS
Abstract

Our study of the synthesis of the aglycone of tiacumicin B is discussed here. We imagined two possible strategies featuring a main retrosynthetic disconnection between C13 and C14. The first strategy was based on Suzuki–Miyaura cross-coupling of 1,1-dichloro-1-alkenes, but the failure of this pathway led us to use a Pd/Cu-dual-catalyzed cross-coupling of alkynes with allenes that had never been implemented before in a total synthesis context. We used density functional theory calculations to guide our strategic choices concerning a [2.3]-Wittig rearrangement step and the final ring-size selective Yamaguchi macrolactonization. This led to two syntheses of the aglycone of tiacumicin B, with one of last generation delivering ultimately an adequately protected and glycosylation-ready aglycone.

Published
2018
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4. Planar Chiral Phosphoric Acids with Biphenylene-Tethered Paracyclophane Scaffolds: Synthesis, Characterization, and Catalytic Screening

Author

Ivo Leito, Jean-François Betzer, Vincent Servajean, Julien Pastor, Angela Marinetti, Pascal Retailleau, Kévin Isaac, Gilles Frison, Karl Kaupmees, Jérémy Stemper, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), University of Tartu, Centre National de la Recherche Scientifique (CNRS), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), and Institute of Chemistry

Subjects
010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Enantioselective synthesis, [CHIM.CATA]Chemical Sciences/Catalysis, Biphenylene, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Characterization (materials science), Catalysis, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Planar, [CHIM]Chemical Sciences, Organic chemistry, Enantiomeric excess
Abstract

International audience; Phosphoric acids with planar chiral paracyclophane scaffolds have been prepared in optically pure form starting from 1,8-dibromobiphenylene, by means of a chiral phosphorodiamidate as the phosphorylating agent. Structural characterization and configurational assignment have been performed by X-ray diffraction studies. The acids promote the organocatalytic enantioselective H-transfer reduction of α-arylquinolines with up to 90% enantiomeric excess.

Published
2014
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5. Aziridines derived from amino acids as synthons in pseudopeptide synthesis

Author

Vincent Servajean, Josiane Thierry, Laidong Song, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
chemistry.chemical_classification, Reaction conditions, 010405 organic chemistry, Chemistry, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Synthon, Regioselectivity, [CHIM.CATA]Chemical Sciences/Catalysis, Aziridine, 010402 general chemistry, 01 natural sciences, Biochemistry, 0104 chemical sciences, 3. Good health, Amino acid, chemistry.chemical_compound, Nucleophile, Drug Discovery, Aspartic acid, Organic chemistry, Reactivity (chemistry)
Abstract

The reactivity of the Z-protected aziridine derived from aspartic acid has been studied with various N- and O-nucleophiles. The optimized reaction conditions allow quick and easy access to 1, 2-diamines or amino alcohols. In the case of opening with N-nucleophiles, very good regioselectivity was observed. Use of an α-amino ester as the nucleophile yielded a methyleneamino pseudodipeptide.

Published
2006
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6. Comportement chimique de quelques atomes de rutherfordium (Rf,Z=104) et dubnium (Db,Z=105) produits a Orsay

Author

G. Ardisson, Jean-François Le Du, Fabiola Monroy Guzman, O. Constantinescu, D. Trubert, Vincent Servajean, M. Hussonnois, Béatrice Weiss, Claire Le Naour, L. Brillard, V. Barci, Youri Oganessian, Institut de Physique Nucléaire d'Orsay (IPNO), Centre National de la Recherche Scientifique (CNRS)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Université Paris-Sud - Paris 11 (UP11), and Robert, Suzanne

Subjects
Dubnium, chemistry, Radiochemistry, Rutherfordium, chemistry.chemical_element, General Chemistry, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], 010501 environmental sciences, 010403 inorganic & nuclear chemistry, 01 natural sciences, 0104 chemical sciences, 0105 earth and related environmental sciences, [PHYS.PHYS.PHYS-CHEM-PH] Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph]
Abstract

Resume Les isotopes 261Rf et 262Db ont ete produits par irradiation de 248Cm par des ions 18O et 19F respectivement a l'aide de l'accelerateur MP Tandem d'Orsay, et isoles en milieu HF grâce au dispositif Rachel. Une nouvelle voie de synthese du radionucleide Db a ete mise en œuvre.

Published
1998

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