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Stereoselective Synthesis of 2-Deoxyoligosaccharides New UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Departamento de Química Analítica y Química Orgánica Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57 Memoria presentada por Andrea Kövér Para optar al título de Doctor en Química Tarragona, Abril 2008 UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Departamento de Química Analítica y Química Orgánica Química Analítica y Química Orgánica de la Universitat Rovira i Virgili. CERTIFICAN: Que el trabajo titulado: “Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57” presentado por Andrea Kövér para optar al grado de Doctor, ha estado realizado bajo su inmediata dirección en los laboratorios de Química Orgánica del Departamento de Química Analítica y Química Orgánica de la Universitat Rovira i Virgili. Tarragona, Abril de 2008 Sergio Castillón Miranda Yolanda Díaz Giménez i UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 AGRADECIMIENTOS UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57 “Querer es tener valor de chocar con los obstáculos.” Stendhal, novelista francés para Ferran iv UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 AGRADECIMIENTOS Éste es el punto donde tradicionalmente va la sección de agradecimientos, pero es tanto lo que debo, y a tantas personas, que es realmente difícil expresarlo en unas pocas líneas. Primero y en muy destacado lugar, quiero agradecer al Dr. Sergio Castillón la confianza que me ha dado durante estos años, tanto dentro como fuera de los laboratorio de síntesis. Al igual que su apoyo en los momentos difíciles y sus consejos sobre la química y la vida. De igual manera, quiero agradecer a la Dra. Yolanda Díaz, que ha tenido la puerta siempre abierta y por haberme ayudado y animado durante estos años. A la Dra. Maribel Matheu sus consejos en los trabajos realizados, su amistad y su ayuda a mantener un ambiente de trabajo agradable y enriquecedor. Por supuesto, a mis compañeros de grupo de investigación: Patricia, David, Miguel, Omar, Antonio, Pep y Isidro. A Núria por nuestras charlas aún después de acabar su tesis doctoral. A los compañeros y profesores poliméricos. En resumen, a todos los integrantes del área de Química Orgánica y en general de Universitat Rovira i Virgili por haber aportado cada uno su granito de arena y hacer que me sintiera como en casa. Al personal del SRC, en especial a Ramón, por su gran ayuda e infinita paciencia con el equipo de resonancia. A mi familia, por haberme dado la educación y los estudios necesarios. A mi familia de aquí, por escucharme y estar a mi lado en los momentos complicados, también gracias a esto hoy estoy escribiendo esta memoria. Por último, a la persona que ha estado a mi lado todo este tiempo sufriendo y disfrutando todos los momentos juntos. Gracias Ferran. v UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 TABLE OF CONTENTS UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57 “Los grandes acontecimientos no corresponden a nuestros momentos bulliciosos, sino a nuestros momentos de tranquilidad.” F. Nietzsche, filósofo alemán viii UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 TABLE OF CONTENTS ABBREVIATIONS xi FIRST Chapter: Introduction and Goals 1 1.1 Introduction 3 1.1.1 Deoxyglycosides 3 1.1.2 Biological Background for the Cardiac Glycosides. Digitoxin 4 1.1.3 Challenges in the Synthesis of 2-Deoxyglycosides 7 1.1.4 Methods for the Synthesis of 2-Deoxyglycosides 8 1.1.4.1 No Control Element at C-2 8 1.1.4.2 Control Element at C-2 11 1.1.5 Synthesis of 2-Deoxyglycosides from Furanoses through an Olefination – Cyclization – Glycosylation Process 17 1.2 Goals 24 SECOND Chapter: Study of the Olefination, Cyclization and Glycosylation of Ribo and Arabino Derivatives 27 2.1.1 Introduction 29 2.1.1 The Need for Synthesis of Novel Phosphine Oxides 29 2.1.2 Previous Methods for the Synthesis of (Sulfanylmethyl)phosphine Oxides 30 2.2 Results and Discussion 31 2.2.1 Synthesis of (Sulfanylmethyl)diphenylphosphine Oxides and Sulfanyl Alkenes 31 2.2.2 Synthesis of Diphenylphosphine Oxides with General Formula Ph2P(O)CH2XR 32 2.2.3 WH Olefination Reactions of Furanoses with Novel Sulfanyl Phosphine Oxides 36 2.2.4 6-Endo Cyclization Reactions from Sulfanyl Alkenes 44, 47 and 51, 53 39 2.2.5 Glycosylation of Cholesterol with the Glycosyl Donors 56 and 57 44 2.3 Conclusions 45 ix UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57 THIRD Chapter: Oxepane Synthesis by 7-endo Electrophile–Induced Cyclization of Alkenylsulfides 49 3.1 Introduction 51 3.2 Results and Discussion 54 3.2.1 Synthesis of Sulfanyl-alkenyl Derivatives from 2,3,4,6-tetra-O-Benzyl- D-glucopyranose 54 3.2.2 Synthesis of Oxepanes Starting from 75 and 83 57 3.3 Conclusions 62 FOURTH Chapter: Synthesis of 2,6-Dideoxyoligosaccharides. Approaches to the Synthesis of Digitoxin and P57 63 4.1 Introduction 65 4.1.1 Chemical Structure of the Digitoxin 65 4.1.2 Previous Syntheses of Digitoxin 67 4.1.3 Chemical Stucture of P57 71 4.1.4 Previous Synthesis of P57 72 4.2 Results and Discussion 74 4.2.1 Retrosynthetic Analysis of Digitoxin and P57 74 rd 4.2.2 Synthesis of the 3 Synthon of P57 77 rd 4.2.3 Synthesis of the 3 Synthon of Digitoxin 79 st nd 4.2.4 Synthesis of the 1 and 2 Synthons of Digitoxin and P57 80 4.2.4.1 Synthesis of Olefination Precursors 80 4.2.4.2 Olefination Reactions 84 4.2.4.3 Cyclization and Glycosylation Reactions: Study of the 5-Endo Cyclization Mode 90 4.3 Conclusions 101 SUMMARY 103 EXPERIMENTAL SECTION 107 x UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 ABBREVIATIONS UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Stereoselective Synthesis of 2-Deoxyoligosaccharides ─ New Approaches to the Synthesis of Digitoxin and P57 “Experiencia es el nombre que damos a nuestras equivocaciones.” Oscar Wilde, escritor irlandés xii UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 ABBREVIATIONS Ac Acetyl ACE Angiotensin-Converting-Enzyme AcOEt Ethyl Acetate AcOH Acetic Acid AIBN 2,2´-Azobisisobutyronitrile All Allyl Bn Benzyl Bp Boiling Point Bu Butyl Bz Benzoyl CAN Ceric Ammonium Nitrate Cat. Catalytic, Catalyst cc. Concentrated CHF Congestive Heart Failure COSY Correlation Spectroscopy CSA Camphore Sulfonic Acid CSIR South African Council for Scientific and Industrial Research d Doublet dd Double Doublet ddd Doublet of Double Doublet δ Chemical Shift DAST Diethylaminosulfur Trifluoride DCM Dichloromethan DDQ 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone DEAD Diethyl Azodacarboxylate DFT Density Functional Theory DIBAL Diisobutylaluminium Hydride DMF N,N-Dimethylformamide DMAP 4-(Dimethylamino)pyridine DNA Deoxy Nucleic Acid Et Ethyl FT–IR Furier Transform – Infra Red Spectroscopy HMBC Heteronuclear Multiple Bond Correlation HOMO Highest Occupied Molecular Orbital HR-MAS High Resolution Magic Angel Spinning HSQC Heteronuclear Single-quantum Correlation xiii UNIVERSITAT ROVIRA I VIRGILI STEREOSELECTIVE SYNTHESIS OF 2-DEOXYOLIGOSACCHARIDES.NEW APRROACHES TO THE SYNTHESIS OF DIGITOXIN AND P-57 Andrea Köver 978-84-691-9523-9 /DL: T-1261-2008 Stereoselective Synthesis of 2-Deoxyoligosaccharides
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