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Total Synthesis of C-Arylglucosidic Ellagitannins

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Total Synthesis of C-Arylglucosidic Ellagitannins Università degli Studi di Ferrara DOTTORATO DI RICERCA IN CoTUTELA con l’UNIVERSITA’ DI BORDEAUX I in Scienze Farmaceutiche CICLO XXII COORDINATORE Prof. Stefano Manfredini Towards the first total synthesis of C-arylglucosidic ellagitannins. A biomimetic approach. Settore Scientifico Disciplinare CHIM/09 Sostenuto il 6 Aprile 2010 In seguito alla valutazione di: Piero PUCCI Professore, Università di Napoli Controrelatore Alessandro PEZZELLA Ricercatore, Università di Napoli Controrelatore Stefan CHAISSANG Ricercatore, Université de Toulouse Referee Doctor Europeus Piet HERDEWIJN Professore, Università di Leuven Referee Doctor Europeus Davanti alla commissione costituita da: Piero PUCCI Professore, Università di Napoli Presidente della Commissione Alessandro PEZZELLA Ricercatore, Università di Napoli Esaminatore Stéphane QUIDEAU Professore, Università di Bordeaux Correlatore di tesi Stefano MANFREDINI Professore, Università di Ferrara Relatore di tesi Stefan CHAISSANG Ricercatore, Université de Toulouse Esaminatore Dottorando Tutore Dott. Natangelo Anna Prof. Manfredini Stefano _______________________________ _____________________________ (firma) (firma) Prof. Quideau Stéphane _____________________________ (firma) Anni 2007/2010 N° d’ordre : 4019 THÈSE en Co-Tutelle PRÉSENTÉE A L’UNIVERSITÉ BORDEAUX 1 ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES par Anna Natangelo POUR OBTENIR LE GRADE DE DOCTEUR SPÉCIALITÉ : CHIMIE ORGANIQUE Vers la première synthèse totale d’ellagitannins C-arylglucosidiques. Une approche biomimétique. Directeur de thèse : Stéphane QUIDEAU Soutenue le : 6 avril 2010 Après avis de : MM. Piero PUCCI Professeur, CEINGE biotecnologie avanzate Rapporteur Alessandro PEZZELLA Directeur de Recherche, Université de Naples Rapporteur Devant la commission d’examen formée de : MM. Piero PUCCI CEINGE Biotecnologie Avanzate Président du jury Alessandro PEZZELLA Directeur de Recherche, Université de Naples Rapporteur Stéphane QUIDEAU Professeur, Universitè de Bordeaux Directeur de thèse Stefano MANFREDINI Professeur, Universitè de Ferrara Co-directeur de thèse Stefan CHAISSANG Maître de Conférences, Université de Toulouse Membre invité Université Bordeaux 1 Les Sciences et les Technologies au service de l’Homme et de l’environnement This study was supported in part by grants from the French-Italian University (Bando VINCI 2008 cap. III) The structure, known but not yet accessible by synthesis, is to the chemist what the unclimbed mountain, the unchartered sea, the untilled field, the unreached planet, are to other men. R.B. Woodward Wonder is the beginning of all science. Aristotele, Metaphysics, I,2,982b Nothing great in the world has been accomplished without passion. F. Hegel Contents List of Abbreviations and Acronyms..................................................................... 12 General Introduction .............................................................................................. 14 Chapter 1 : Ellagitannins Structural Description and Total Synthesis .......17 1.1 Ellagitannins : a class of bioactive plant polyphenols.................................... 18 1.2 C-Glucosidic ellagitannins : A special subclass of ellagitannins................... 24 1.3 Biological activity of C-glucosidic ellagitannins ............................................. 30 1.4 Ellagitannins Total Synthesis........................................................................... 32 1.5 HHDP-formation via oxidative biaryl coupling (Method A) ........................ 37 1.5.1 Total synthesis of tellimagrandin I and II (4,6-HHDP) ....................................... 37 1.5.2 Total synthesis of sanguiine H-5 (2,3-HHDP)...................................................... 39 1.5.3 Total synthesis of pedunculagin (2,3,4,6-HHDP)................................................. 40 1.5.4 Ullmann Coupling.................................................................................................. 41 1.5.5 Total synthesis of corilagin (3,6-HHDP)............................................................... 44 1.5.6 The strategy of Spring for the synthesis of sanguiin-H5...................................... 46 1.5.7 PIFA mediated oxidative coupling attempts.......................................................... 47 1.6 Enantiomerically pure Ellagitannins via double esterification of hexahydroxydiphenic acid (Method B) ........................................................... 48 1.6.A Enantioselective synthesis of a group (S)-HHDP ................................................ 49 1.6.B Kinetic resolution................................................................................................... 51 1.6.1 Total synthesis of strictinin (4,6-HHDP)............................................................... 52 1.6.2 Total synthesis of gemine D, hippomanin A and 1,3-di-O-galloyl-4,6-O-(S)- hydroxydiphenoyl--D-glucopyranoside (4,6-HHDP)................................................... 54 1.6.3 Total synthesis of praecoxin B, pterocarinin C, pariin M and mahtabin A (2,3- HHDP)............................................................................................................................. 55 1.6.4 Khanbabee’s pedunculagin (2,3,4,6-HHDP) total synthesis................................ 58 1.7 Hemisynthesis of a C-arylglucosidic ellagitannin .......................................... 59 Chapter 2 : Retrosynthetic Analysis and Precursors Synthesis ...................60 2.1 Retrosynthetic analysis ..................................................................................... 62 2.2 Synthesis of intermediate D.............................................................................. 65 2.2.1 Synthesis of polyhydroxylated intermediate D3..................................................... 65 2.2.2. Synthesis of sugar E.............................................................................................. 66 2.2.3. “Biomimetic” approach to the D3 synthesis: esterification of the sugar E with gallic acid......................................................................................................................... 68 2.2.4 Synthesis of completely protected galloyl units F0 ................................................ 70 2.2.5 Preparation of intermediates D0 ............................................................................ 71 2.2.6 Preparation of the itermediates D3 via orthogonal deprotection of precursors D0 .......................................................................................................................................... 72 Contents 2.2.7 Synthesis of para-protected galloyl units F2.......................................................... 74 2.2.8 Preparation of intermediates D2 ............................................................................ 75 2.2.9 Protection of F2 units ............................................................................................. 76 2.2.10 Preparation of intermediates D2’ ......................................................................... 77 2.2.11 Preparation of the intermediates D2 via orthogonal deprotection of D2’ ........... 78 2.3 Synthesis of inetrmediates B ............................................................................ 79 2.4 Intermediates B via Biarylic oxidative coupling ............................................ 80 2.4.1. o-chloranil mediated intramolecular biarylic oxidative coupling ....................... 80 2.4.2 o-chloranil mediated oxidative coupling of 135b.................................................. 85 2.4.3 o-chloranil mediated oxidative coupling of 135d.................................................. 87 2.4.4 Cu(II)-amine complex promoted intramolecular biarylic oxidative coupling..... 88 2.4.5 Cu(II)-amine complex mediate oxidative coupling of 149b ................................. 91 2.5 Intermediates B via acetylation of a racemic unit (±)-HHDP....................... 93 2.5.1 Synthesis of the racemic (±)-HHDP...................................................................... 94 2.5.2 Installation of the HHDP unit on the sugar E...................................................... 95 Chapter 3 : C-arylglucosidation Step............................................................100 3.1 The key step of C-arylglucosidation .............................................................. 101 3.2 Our approach to C-arylglucosidation............................................................ 103 3.3 First C-arylglucosidation attempts: Tanaka’s conditions .................... 106 3.3.1 C-arylglucosidation on the architecture B (HHDP-bearing)............................. 106 3.3.2 C-arylglucosidation on the architecture D (two galloyl not coupled) ................ 107 3.4 C-arylglucosidation attempts in organic solvents ........................................ 108 3.5 C-arylglucosidation attempts in acid conditions on the architecture B ..... 109 3.6 The C-arylglucosidation step.......................................................................... 112 3.6.1 Reaction on (S)-158 work-up and products purification.......................... 112 3.6.2 Products 175 and characterization ................................................................ 114 3.6.3 C-1 configuration determination ......................................................................... 119 3.7 C-arylglucosidation on the architecture D.................................................... 121 3.8 C-arylglucosidation attempts in acid conditions on a completely deprotected intermediate
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