WorldCat Identities

Zhu, Jieping (1965-....).

Overview
Works: 35 works in 36 publications in 2 languages and 43 library holdings
Classifications: QD501, 547.2
Publication Timeline
Key
Publications about  Jieping Zhu Publications about Jieping Zhu
Publications by  Jieping Zhu Publications by Jieping Zhu
Most widely held works by Jieping Zhu
Multicomponent reactions ( Book )
2 editions published between 2005 and 2006 in English and held by 8 WorldCat member libraries worldwide
In the very first book on this hot topic, the expert editors and authors present a comprehensive overview of these elegant reactions. From the contents: Organoboron compounds; Free-radical mediated multicomponent coupling reactions; Applications in drug discovery; Metal catalyzed reactions; Total synthesis of natural products; Asymmetric isocyanide-based reactions; The Biginelli reaction; Asymmetric isocyanide-based reactions; The Domino-Knoevenagel-Hetero-Diels-Alder Reaction and related transformations; Catalytic asymmetric reactions; Algorithm based methods for discovering novel reactions
Approche vers la synthèse totale de la lipiarmycine Utilisation de para-nitrophénylsulfones dans la réaction de Julia modifiée ; Synthèse monotope d'alpha-cétoamides via une nouvelle réaction à quatre composants by Jean-Marie Grassot ( Book )
1 edition published in 2007 in French and held by 2 WorldCat member libraries worldwide
The first part of this thesis was to develop an approach towards the synthesis of lipiarmicin. This macromolecule possesses interesting antibiotic properties and no total synthesis has been already described. Lipiarmicin contains two carbohydrate units and an aglycon. The works presented in this thesis concern the synthesis of the aglycon part which is a 18-membered macrolactone. The formations of five asymmetric centers, two (E),(E) conjugated diene systems and a trisubstitued trans olefin have to be controlled. A strategy based on the elaboration of two principal synthons A and B, has been imagined and explored. Synthons A and B could be connected via a Julia type reaction to build up the trisubstituted olefin and a Yamagushi type macrolactonisation would lead to the desired macrolactone. Thanks to important transformations such as Stille-type couling or Evans aldolisation, we could obtain synthon A and a direct precursor of synthon B. In a second part, and in parallel to the first part, we developed a new version for the modified Julia reaction, which implies the use of para-nitrophenylsulfones. Thanks to this practical method, a library of olefins has been synthesized from aromatic aldehydes with moderate to excellent yields and with good to high stereoselectivities, especially in the case of the fully-stabilised sulfones. In the last part, we described a new synthesis of [alpha]-ketoamides based on a four components reaction between an aldehyde, a hydroxylamine, an isonitrile and acetic acid, in presence of molecular sieves. This transformation allowed us to synthesise several ketoamides with different structures, in moderate yields
Réactions de passerini et d'ugi dans des conditions oxydantes et approche vers la synthèse totale de la (-)-norsuaveoline by Tifelle Ngouansavanh ( Book )
1 edition published in 2008 in French and held by 1 WorldCat member library worldwide
This scientific project focuses in particular on the development of new reactions tandem, combining oxidation process and multi-component reactions and on the approach towards total synthesis of (-)-norsuaveoline. In the first part of this work, we have developed a new concept: the oxidative Passerini reaction in the presence of IBX. The reaction is carried out in mild conditions and provided a wide variety of alpha-acyloxycarboxamides in one step. Primary alcohol is an efficient partner in the oxidative Passerini reaction and this methodology has demonstrated the potential of such a process, particularly when the aldehyde is unstable or difficult to handle. Then, this concept has been extended to the Ugi reaction and allowed a dual acylation of nitrogen and alpha-carbon centers of tetrahydroisoquinoline and provided Csp3-Csp2 bonds in one step. Morever this tandem oxidation / UGI reaction is particularly rapid and efficient for the synthesis of polypetides, without the use of peptide-coupling agents and protection / deprotection steps. Eventually, the second part of this research project described our approach towards the total synthesis of an alkaloid : the (-)-norsuaveoline. The original and synthetic approach based on modular construction of the molecule from the right side starting from L-(-)-glutamic acid, and a late formation of indole nucleus by a palladium catalysed heteroannulation with substituted o-iodoanilines. During this work, we validated three key-steps of the synthesis : formation of oxazole with lithiated methylisocyanide, intramolecular Kondrat'eva reaction leading to a trisubstituted pyridine and formation of a indole derivative with a palladium catalysed heteroannulation already developed in our laboratory
Synthèse asymétrique de l'acide actinoïdique; vers la synthèse totale de RP66453 : Synthèse à haut débit d'aryl triflates et d'aryl nonaflates by Sabine Boisnard ( Book )
1 edition published in 2001 in French and held by 1 WorldCat member library worldwide
The complex molecular architecture of Vancomycin and the recent emergence of the vancomycin-resistance phenomenon have rendered it an attractive synthetic target for chemists. In connection with our work aimed at developing a new strategy towards the construction of the ABCOD ring, an efficient synthesis of actinoidic acid common to all the antibiotics belonging to the vancomycin family was required. The first part of this report deals with the synthesis of actinoidic acid, which applies the Meyer's reaction to build the aryl-aryl bond. The other key step is the Strecker reaction based on the use of a sulfinimine as a chiral auxiliary in order to introduce a chiral amino acid. In the second part, we have studied the synthesis of RP66453, a neurotensin antagonist, it could be useful in the treatment of nervous diseases such as Alzheimer's and Parkinson's. Its structure is similar to that of vancomicyne and the main stuctural feature if this natural product is the presence of two macrocycles with an aryl-aryl and an aryl-aryl bond
Organocatalyse asymétrique de la réaction d'aza-Morita-Baylis-Hillman by Nacim Abermil ( Book )
1 edition published in 2010 in French and held by 1 WorldCat member library worldwide
The aim of this study is the development of a highly enantioselective aza-Morita-Baylis-Hillman reaction catalyzed by [beta]-isocupreidine derivatives. First, new bifunctional organocatalysts have been synthesized and efficiently applied to the aza-MBH transformation involving [beta]-naphthyl acrylate. Indeed, high yields and enantioselectivities have been achieved and the presence of a catalytic amount of [beta]-naphthol appears to be essential to the reaction success. Moreover, aliphatic imines have been converted with excellent stereocontrol for the first time. Next, it has been discovered that [beta]-naphthol, an achiral protic additive, was able to invert the enantioselectivity of the aza-MBH transformation ln the case of alkylvinylketones. Then, the use of [alpha]-amidosulfones as imine surrogates allow to increase both efficiency and asymmetric induction of the aza-MBH reactio in the case of aliphatic imines. Finally, in order to try to better understand the transformation process, a molecular modelling study has been conducted with Dr Élise Tran
Développement de nouvelles réactions multi-composants pour la synthèse de polyhétérocycles polysubstitués by Aude Fayol ( Book )
1 edition published in 2004 in French and held by 1 WorldCat member library worldwide
The scientific project consisted in developing new multi-components reactions (MCR) for the synthesis of polyheterocycles of very varied structures. For that, we emphasized the synthesis with three component of 5-amino-oxazoles developed by the laboratory starting from an aldehyde, an amine and a isocyanoacetamide. The use of the reactivity of this platform amino-oxazole and in particular its dienic character, made it possible to extend considerably the field of this new MCR. The introduction of a dienophile to one of the starting material made it possible to carry out an intramolecular reaction of cycloaddition. The variation of the nature and the site of the dienophile led to the synthesis of various polyheterocycies like : furoquinolines, tetrahydrofuropyridines, oxa-bridged tetrahydroquinolines, diazaphenanthrenes, tetrahydronaphthyridines, 6-azaindolines as well as tetrahydroquinolines
Synthèse totale de la biphénomycine B by Renaud Lépine ( Book )
1 edition published in 2005 in French and held by 1 WorldCat member library worldwide
The biphenomycin B is a natural product presenting an interesting antibiotic activity. We established a new total synthesis of this molecule, short and convergent, calling upon a key step of closing the macrocycle by formation of the aryl-aryl bond using an intramolecular Suzuki reaction or by application of a tandem Miyaura-Suzuki reaction. For that, different tripeptides, linear precursors of the macrocycle, have been synthesized. Themselves were obtained starting from classical peptide couplings of three non-proteinogenic amino acids. A highly enantioselective and effective synthesis of two of them, derived from (S)-2-isopropyloxy-6-iodophenylalanine, as well as a modification of their skeletons in order to obtain six variously protected amino acids and comprising either an ester boronic or an iodine atom on the aromatic ring, was carried out. The central amino acid of the biphenomycin B, (2S,4R)-4-hydroxyornithine, was obtained by using the diastereoselective alkylation of Schöllkopf's reagent after a failure in using the asymmetrical PTC methodology. Then, formation of the aryl-aryl bond with the concomitant formation of the 15-membered meta, meta-cyclophane was carried out by using an intramolecular Suzuki-Miyaura marocyclisation procedure, with the help of the microwaves methodology. Finally synthetic studies on the basis of (R)-[beta]-trichlorométhyl-[beta]-propiolactone were carried out in order to realize the synthesis of various natural products
Synthèse de macrocycles par réaction multi-composants by Christopher Housseman ( Book )
1 edition published in 2006 in French and held by 1 WorldCat member library worldwide
Résumé français
SYNTHESE TOTALE DE K 13 (INHIBITEUR DE L'E.C.A.) ET DE RA VII (ANTICANCEREUX) ; DEVELOPPEMENT D'UN NOUVEAU REACTIF DE TRANSFERT DU GROUPE TRIFLATE : LE TRIFLATE DE 4-NITROPHENOL by ANTONY BIGOT ( Book )
1 edition published in 1998 in French and held by 1 WorldCat member library worldwide
MON TRAVAIL DE THESE A EU POUR BUT DE DEVELOPPER UNE NOUVELLE METHODE DE FORMATION DE LA LIAISON BIARYLETHER CAPABLE DE REPONDRE A PLUSIEURS CRITERES : NECESSITE DE CONDITIONS DOUCES ; RENDEMENTS ELEVES ; POSSIBILITE D'APPLIQUER CETTE METHODE DE MANIERE INTRAMOLECULAIRE, AFIN DE REALISER LA MACROCYCLISATION PAR FORMATION DE LA LIAISON BIARYLETHER. DANS LA PREMIERE PARTIE NOUS AVONS MONTRE QUE LE SYSTEME O-FLUORONITROARYLE SUBIT L'ATTAQUE D'UN PHENOLATE POUR CONDUIRE AU BIARYLETHER CORRESPONDANT AVEC DES RENDEMENTS DE L'ORDRE DE 80 %. LA VERSION INTRAMOLECULAIRE NOUS A PERMIS DE REALISER LA FERMETURE DU MACROCYCLE A 17 CHAINONS DE K 13 AVEC DES RENDEMENTS SUPERIEURS A 80 % ET SANS QU'IL SOIT NECESSAIRE D'OPERER DANS DES CONDITIONS DE HAUTE DILUTION. NOUS AVONS AINSI PU REALISER UNE SYNTHESE TOTALE TRES EFFICACE DE K 13. NOUS AVONS DECOUVERT QUE LORSQU'UN SUBSTRAT CONTIENT DEUX FONCTIONS PHENOL DE REACTIVITE EQUIVALENTE, SEUL LE MACROCYCLE DESIRE META-PARA CYCLOPHANE A 17 CHAINONS EST FORME AUX DEPENS DU MACROCYCLE PARA-PARA CYCLOPHANE A 18 CHAINONS, UNE PROPRIETE INHERENTE A LA REACTION INTRAMOLECULAIRE. DANS LA SECONDE PARTIE, NOUS AVONS REALISE LA SYNTHESE DU MOTIF STRUCTURAL CYCLOISODITYROSINE, MACROCYCLE A 14 CHAINONS FAISANT PARTIE DE LA STRUCTURE DE RA VII. DES PROBLEMES D'EPIMERISATION AYANT ETE RENCONTRES, NOUS AVONS DU CHANGER DE STRATEGIE PAR CHANGEMENT DE POSITION DU GROUPE NITRO, CE QUI NOUS A CONDUIT A UNE SYNTHESE TRES EFFICACE DE LA CYCLOISODITYROSINE. ICI ENCORE, NOUS AVONS OBSERVE QUE SEUL LE MACROCYCLE REGIOISOMERE META-PARA CYCLOPHANE A 14 CHAINONS EST PRODUIT ET UNE TENTATIVE D'EXPLICATION DE CETTE SELECTION A ETE PROPOSEE SUR LA BASE DE CALCULS DE MODELISATION MOLECULAIRE. AVEC CETTE VOIE DE SYNTHESE EFFICACE DE LA CYCLOISODITYROSINE, NOUS AVONS PAR LA SUITE REALISE LA SYNTHESE TOTALE DE RA VII. DANS LA TROISIEME PARTIE, NOUS AVONS DEVELOPPE UN NOUVEAU REACTIF DE TRANSFERT DU GROUPEMENT TRIFLATE SUR LES PHENOLS : LE TRIFLATE DE 4-NITROPHENOL
Approche vers la synthèse totale de l'ecteinascidine 743 by Michaël De Paolis ( Book )
1 edition published in 2003 in French and held by 1 WorldCat member library worldwide
The ecteinascidins, a family of tetrahydroisoquinoline alkaloids isolated from the Carribean tunicate Ecteinascidia turbinate, possess potent cytotoxic activity against a variety of tumor cell lines in vitro and against several rodent tumors and human tumor xenografts in vivo. One of its members, the ecteinascidine 743 is currently in phase II/III clinical trials as an anticancer agent. The potent antitumor activities in conjunction with the molecular - complexity and the lack of availability have made Et 743 an attractive synthetic target. In this context, we have been investigated a short and convergent approach to the total synthesis of Et 743. We have developed an efficient route to the central tetrahydroisoquinoline containing a 1,4-bridged 10-membered macrolactone by using phenolic aldol reaction, subsequent Pictet-Spengler cyclization under newly developed conditions. The right fragment of Et 743 derived of L-DOPA was prepared by an asymmetric alkylation using cinchonidium salts as a chiral phase transfert catalyst. The coupling between the two fragments was made by a modified Strecker reaction and after few steps including acid initiated macrocyclization on benzylic position, an advanced intermediate of Et 743 is obtained. N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides is also described
Approches de la synthèse totale de la (-)-lémonomycine by Guillaume Bernadat ( Book )
1 edition published in 2009 in French and held by 1 WorldCat member library worldwide
Lemonomycin is a member of the tetrahydroisoquinolin antitumor antibiotics family. Its structure features a highly substituted tetrahydroisoquinolin, as well as a diazabicyclo[3.2.1]octane system. An aminosugar moiety is also present in the structure. After a short review of existing synthetic works towards lemonomycin and structurally related molecules, several synthetic routes towards this natural product are envisioned and their implementation is disclosed. A method to prepare the pyrrolidine ring through an allylsilane amidoalkylation reaction is first presented. This method is then applied in different strategies towards lemonomycin. Some routes begin with the formation of the tetrahydroisoquinoline ring system by a Pictet-Spengler reaction. Different types of internal nucleophiles are then tested in order to build the bridged bicyclic system. In other routes, the diazabicyclo[3.2.1]octane core is built first. Several strategies are then tried in order to couple the aromatic moiety required for the tetrahydroisoquinoline: phenolic type Mannich reaction, phenolic type aldol reaction, benzyle bromide N-alkylation. Eventually, a stereocontrolled synthesis of the 2,6-dideoxy-4-amino sugar from D-threonine is presented
Etude de nouvelles voies d'accès a coeur pentacyclique des ecteinascidines et synthèse d'analogues by Nicolas Demoulin ( Book )
in French and held by 1 WorldCat member library worldwide
Les ecteinascidines sont une famille de tétrahydroisoquinoléines d'origine marine aux propriétés anticancéreuses très prometteuses. La molécule la plus pluissante, l'ecteinascidine 743, est d'ailleurs commercialisée depuis 2007 en Europe sous le nom de Yondelis® dans le cadre du traitement de sarcomes avancés des tissus mous. En outre, ces composés constituent une nouvelle classe d'agents antitumoraux grâce à un mécanisme d'action original encore en cours d'investigation. La découverte d'analogues simplifiés de l'ecteinascidine 743, en particulier la phtalascidine et le Zalypsis®, n'ont fait que confirmer les nombreuses perspectives offertes par ces molécules. L'objectif de cette thèse était donc de développer de nouvelles voies d'accès à des analogues inédits d'ecteinascidines, en s'appuyant sur les synthèses totales des ecteinascidines 743 et 597 mises au point au laboratoire. Ces travaux nous ont d'abord menés à l'élaboration d'une nouvelle stratégie à partir de L-tyrosine pour la synthèse de la tétrahydroisoquinoléine droite commune aux différentes ecteinascidines. Ensuite, d'autres voies de synthèse du cœur pentacyclique de l'ecteinascidine 743 ont été étudiées, et en particulier, une réaction clé de N-alkylation diastéréosélective entre une amine énantiomériquement pure et un 2-aryl-2-bromoacétate racémique. Enfin, c'est en s'appuyant sur les synthèses totales des ecteinascidines 743 et 597 que la synthèse de deux plates-formes a été effectuée donnant accès aux analogues d'ecteinascidines désirés
Synthèse et fonctionnalisation d'hétérocycles azotés catalysées par les métaux de transition. Approche vers la synthèse totale de la (-)-norsuavéoline by Sébastien Bénard ( )
1 edition published in 2011 in French and held by 1 WorldCat member library worldwide
Ces travaux de thèse traitent de la synthèse et de la fonctionnalisation d'hétérocycles azotés catalysées par les métaux de transition. La première partie de ce projet a été consacrée à la mise en place d'une méthode simple et efficace pour la N-cyclopropylation de différents composés azotés. A partir de l'acide cyclopropylboronique, en présence de sels de cuivre et dans des conditions de couplage oxydant, une grande variété de composés azotés ont pu être N-cyclopropylés. Cette méthode permet une nouvelle voie d'accès aux substrats N-cyclopropylés.La deuxième partie de ces travaux de thèse porte sur l'étude de la synthèse de benzimidazole. Ces hétérocycles azotés ont pu être obtenus à partir d'amidines grâce à une séquence réactionnelle faisant intervenir une réaction de N-arylation suivi d'une cyclisation via la fonctionnalisation d'une liaison C-H.La troisième partie de ce manuscrit se focalise sur la synthèse de pyrroles. Cette famille de composés est réputée pour son abondance dans les molécules biologiquement actives. Nous avons développé une réaction séquentielle monotope, permettant la synthèse de N-H pyrroles poly-fonctionnalisés via la formation d'un énaminone, catalysée par de l'indium (III), suivi d'une étape d'hétéroannulation catalysée par du palladium.Enfin, la dernière partie de ce projet scientifique décrit notre approche vers la synthèse totale d'un alcaloïde : la (-)-norsuavéoline. L'originalité de notre approche est basée sur la synthèse, dans un premier temps, du noyau pyridinique de la molécule à partir de l'acide L-(-)-glutamique, pour finir par la formation tardive du noyau indolique. Jusqu'à maintenant, nous avons développé et optimisé la synthèse de la pyridine. Des études sont toujours en cours au laboratoire afin de former la partie indolique et de terminer cette synthèse
La réaction de Strecker dans des conditions oxydantes synthèse et applications des alpha-iminonitriles by Patrice Fontaine ( Book )
1 edition published in 2009 in French and held by 1 WorldCat member library worldwide
L'axe majeur de ces travaux de thèse est l'étude de la réaction trois composants de type Strecker en conditions oxydantes. Cette étude nous a permis de développer dans un premier temps des méthodes d'accès efficaces aux [alpha]-iminonitriles à partir d'alcools, d'aldéhydes, et d'amines. La réactivité des [alpha]-iminonitriles a dans un second temps été étudiée. Ainsi, une méthode générale d'amidification d'alcools a été développée mettant en jeu une transformation simple de ces composés. De plus, nous avons également élaboré un accès rapide en deux étapes aux indolizidines et aux 2-aminopyrroles via respectivement des cycloadditions de type [4+2] intramoléculaires et des cycloadditions de type [4+1] intermoléculaires à partir d'[alpha]-iminonitriles [beta],[gamma]-insaturés. Finalement, des perspectives intéressantes ont été validées via la réduction enantiosélective organocatalysée d'[alpha]-iminonitriles et via leur utilisation comme accepteur de Michaël en présence de thiol
Synthèse énantiosélective d'1,2 et 1,3-diamines et Développement de réactions multicomposants dans des conditions oxydantes by Fleur Drouet ( )
1 edition published in 2011 in French and held by 1 WorldCat member library worldwide
The aim of this study is the development of new access to highly functionalized nitrogen-containing compounds with respect to the green chemistry principles.First, an Ugi four-component reaction from alcohols has been studied. In the presence of hypervalent iodine compounds, used as oxidant and introduced in stoechiometric or catalytic quantites, an efficient one-pot sequence has been developed.Then, a new four-component Mannich reaction using a catalytic amount of BINOL-derived phosphoric acid gave an access to enantioenriched 1,3-diamines from enamides. Changing the electrophilic imine partner to a diazene compound afforded aminoketones or 1,2-diamines precursors in high yields and excellent enantiomeric excess.Finally, two new iron-catalyzed multicomponent reactions of enamides with TEMPO and various nucleophiles provided an efficient synthesis of aminoalcohols derivatives. These domino reactions involving an oxidative process from enamides offered a convenient and economical method to establish two C-O bonds in a single operation
Etude de la réaction de Povarov synthèse énantiosélective de composés diaminés organocatalysée par des acides phosphoriques chiraux by Guillaume Dagousset ( )
1 edition published in 2011 in French and held by 1 WorldCat member library worldwide
This work deals with the Povarov reaction, an inverse electron-demanding Diels-Alder reaction between 2-aza-dienes (generally an N-aryl-imine) and a dienophile such as an electron-rich olefin, leading to the formation of tetrahydroquinolines. We were able to perform this reaction in a multicomponent way, ie by the in situ formation of the imine from the corresponding aldehyde and aniline. Moreover, this multicomponent reaction was also énantiosélective, by using chiral phosphoric acids as catalysts, and by choosing enecarbamates as diénophiles, which could interact with the catalyst thanks to their N-H bond. This methodology allowed to synthesize 4-amino-tetrahydroquinolines in good yields with total diastereoselectivities and excellent enantioselectivities. The use of ene-thioureas as dienophiles also allowed to synthesize hexahydropyrroloquinolines with the same selectivities, following the same method.We also studied the mechanism of this Povarov reaction. We proved that it is a stepwise mechanism, by trapping the iminium intermediate, either via an intermolecular reaction with ethanol leading to chiral 1,3-diamines, or via an intramolecular reaction in the particular case of phenylacetaldehyde, then leading to 1,3-diaminotetralins
Activation d'un acide carboxylique terminal via un oxazole interne by Carine Bughin ( Book )
1 edition published in 2005 in French and held by 1 WorldCat member library worldwide
We have developed a novel macrolactonization technology. It is a domino process in which a strategically incorporated 5-amino oxazole serves as an internal traceless activator of the neighboring C-terminal carboxylic acid. No coupling reagent is required and the entire sequence is triggered by just a few equivalents of trifluoroacetic acid under very mild conditions. This new methodology has been successfully applied for the synthesis of cyclodepsipeptides and cyclic aminosugars. By combinaison with a three-component synthesis of 5-amino oxazole, a two-step synthesis of structurally complex cyclodepsipeptides, tripeptides and cyclic aminosugars from readily accessible starting materials is developed. An additional study of the mechanism of this domino process has also been provided
<> by Pierre Cristau ( Book )
1 edition published in 2003 in French and held by 1 WorldCat member library worldwide
DANS LA PREMIÈRE PARTIE DE CE MANUSCRIT, NOUS AVONS DECRIT LA PREMIÈRE SYNTHÈSE TOTALE DES MAURITINES A, B, C ET F, ALCALOÏDES CYCLOPEPTIDIQUES À 14 CHAÎNONS BIOLOGIQUEMENT ACTIFS. LA STRATÉGIE DE SYNTHÈSE QUE NOUS AVONS DÉVELOPPÉ EST BASÉE SUR UNE CYCLOÉTHERIFICATION PAR RÉACTION DE S(N)AR INTRAMOLÉCULAIRE ET MET EN JEU UN TRIPEPTIDE LINÉAIRE INTACT, CE QUI REND LA STRATÉGIE TRÈS CONVERGENTE. LE RENDEMENT GLOBAL DE CES SYNTHÈSES TOTALES EST DE 6.7-10.2 POUR CENT POUR 13-14 ÉTAPES. UNE ÉTUDE COMPLÈTE PAR SPECTROSCOPIE RMN A ÉTÉ RÉALISÉE SUR LES MAURITINES A, B, C ET F, PERMETTANT NOTAMMENT D'ATTRIBUER, POUR LA PREMIÈRE FOIS, TOUS LES SIGNAUX CORRESPONDANT AUX PROTONS MAIS AUSSI À TOUS LES CARBONES. DANS LA DEUXIÈME ET TROISIÈME PARTIE DE CE MANUSCRIT, NOUS AVONS DÉCRIT UNE NOUVELLE SÉQUENCE UGI-S(N)AR PERMETTANT DE SYNTHÉTISER EFFICACEMENT DES MACROCYCLES, ANALOGUES DE PRODUITS NATURELS BIOLOGIQUEMENT ACTIFS, QUI COMPORTENT SOIT UN MOTIF BIARYL ÉTHER SOIT UN MOTIF ARYL-X-ALKYL ENDOCYCLIQUE (X = NH, 0, S). CETTE SÉQUENCE PERMET D'INTRODUIRE UNE GRANDE DIVERSITÉ STRUCTURALE DANS LES MOLÉCULES CIBLES ET DES MACROCYCLES À 14, 15, 16 ET 17 CHAÎNONS ONT PU ÊTRE SYNTHÉTISÉS. ENFIN, LA SÉQUENCE UGI-S(N)AR PERMETTANT D'ACCÉDER AUX MACROCYCLES COMPORTANT UN MOTIF BIARYL ÉTHER A PU ÊTRE APPLIQUÉE AUSSI EFFICACEMENT SUR SUPPORT SOLIDE (RÉSINE DE WANG). DANS LA DERNIÈRE PARTIE DE CE MANUSCRIT, NOUS AVONS CONÇU ET SYNTHÉTISÉ UN NOUVEAU CYCLOPHANE DE TYPE CYCLOISODITYROSINE, SUPPORT EXTERNE POTENTIEL D'UN COUDE BÉTA. AINSI, QUATRE MOLÉCULES CIBLES ONT ÉTÉ SYNTHÉTISÉES PUIS ENTIÈREMENT CARACTÉRISÉES. UNE ANALYSE CONFORMATIONNELLE DÉTAILLÉE (RMN, DICHROÏSME CIRCULAIRE) A MONTRÉ QUE CETTE UNITÉ CYCLOISODITYROSINE CONSTITUE VRAISEMBLABLEMENT UN BON SUPPORT EXTERNE D'UN COUDE BÉTA DU TYPE II, QUI POURRAIT PERMETTRE LE DÉVELOPPEMENT D'UNE NOUVELLE CLASSE DE PEPTIDOMIMETIQUES
Synthèse asymétrique de dérivés de l'histrionicotoxine et de spiropipéridines apparentées by Jieping Zhu ( Book )
1 edition published in 1991 in French and held by 1 WorldCat member library worldwide
NOUS PRESENTONS DANS UNE PREMIERE PARTIE UNE NOUVELLE VOIE D'ACCES A LA SYNTHESE ASYMETRIQUE DES 1,2-DIAMINES CHIRALES. ELLE EST BASEE SUR L'ADDITION CHIMIOSELECTIVE DES ORGANOLITHIENS OU ORGANOCUPRATES SUR LE SYNTHON 2-CYANO-6-PHENYLOXAZOLO-PIPERIDINE POUR CONDUIRE A UNE IMINE INTERMEDIAIRE QUI APRES REDUCTION PERMET L'ACCES AUX DIFFERENTES 1,2-DIAMINES CHIRALES. CE RESULTAT A ETE APPLIQUE A LA SYNTHESE ASYMETRIQUE D'UN ANALOGUE DE LA TETRAPONERINE. LA DEUXIEME PARTIE DE CETTE THESE CONCERNE LA SYNTHESE ASYMETRIQUE D'UNE NOUVELLE STRUCTURE 1,8-DIAZASPIRO (5,5) UNDECANE QUI PRESENTE UN SQUELETTE HYBRIDE ENTRE CEUX DE L'HISTRIONICOTOXINE ET DES ALCALOIDES DU GENRE NITRARIA. TROIS VOIES DIFFERENTES ONT ETE DEVELOPPEES PERMETTANT LA SYNTHESE DE CINQ COMPOSES DANS CETTE SEIE, QUI DIFFERENT PAR LA PRESENCE DES CHAINES LATERALES, AINSI QUE PAR LA STEREOCHIMIE DES CARBONES QUI LES PORTENT. LES CONFIGURATIONS RELATIVES ET ABSOLUES DES COMPOSES PREPARES ONT ETE DETERMINEES PAR DES ANALYSES CONFORMATIONNELLES ET PAR DES ETUDES APPROFONDIES EN RMN DU #1H (COSY, #1H-#1H, NOE-DIFF, NOESY) ET DU #1#3C (COSY #1#3C-#1H, COLOC). MALGRE LES NOMBREUX TRAVAUX EXISTANT DANS LA LITTERATURE SUR LA SYNTHESE DE LA ()-PERHYDROHISTRIONICOTOXINE (PHTX), IL N'EXISTE QUE PEU DE RESULTATS EN SERIE OPTIQUEMENT ACTIVE. NOUS AVONS REALISE, DANS LA TROISIEME PARTIE, UNE SYNTHESE ASYMETRIQUE DE LA (-)-DEPENTYL-PHTX, AINSI QUE LA (-)-2-EPI-PHTX EN 13 ET 12 ETAPES RESPECTIVEMENT. UNE ALDOLISATION INTRAMOLECULAIRE A ETE EXPLOITEE POUR CONDUIRE LE SQUELETTE AZASPIRANNIQUE
Réactions dominos et réactions multi-composants catalysées au palladium by Artur Pinto ( Book )
1 edition published in 2007 in French and held by 1 WorldCat member library worldwide
The scientific project involved the development of new palladium catalyzed domino and multi-components reaction for heterocycles synthesis. First we have described a new synthesis of physostigmine which relies on a domino Heck / cyanation reaction key step. An asymmetric version of this reaction has also been developed. In a second part, we have developed a synthesis of 3-(diarylmethylene)oxindoles by a carbopalladation / CH activation / arylation domino process from easily accessible products. Then, with the success of this reaction, two multi-component reactions have been devised. The first one combines a Sonogashira reaction with the carbopalladation / CH fonctionalisation, the second one combines a alladium catalysed amidation reaction with the same domino reaction. During the development of the last domino sequence, we have uncovered a new way to synthesize 6-aryluracil: the synthesis involved a simple dimerisation reaction of 3-arylpropynamide. In the last part, we have carried out preliminary studies to develop a new dihydropyrrole multi-component synthesis using the reactivityof isonitrile and allyl
 
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