Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience

INDICE: Preface Zbigniew J. Witczak & Roman Bielski .Foreword Samuel Danishefsky .1. Introduction to Asymmetric Domino Reactions Pellissier Hélène .1.1 Introduction .1.2 Asymmetric Domino Reactions Using Chiral Carbohydrate Derivatives .1.2.1 Stereocontrolled Domino Reactions of Chiral Carbohydrate Derivatives .1.2.2 Enantioselective Domino Reactions Catalysed by Chiral Carbohydrate Derivatives .1.3 Conclusions .References .2. Organocatalyzed Cascade Reaction in Carbohydrate Chemistry Benjamin Voigt and Rainer Mahrwald .Abstract .References .3. Reductive Ring–opening in Domino Reactions of Carbohydrates Raquel G. Soengas, Sara M. Tomé and Artur M. S. Silva .Abstract .3.1 Introduction .3.2 Bernet–Vasella reaction .3.2.1 Domino reductive fragmentation/ reductive amination .3.2.2 Domino reductive fragmentation/ Barbier–type allylation .3.2.3 Domino reductive fragmentation / Barbier–type propargylation .3.2.4 Domino reductive fragmentation / vinylation .3.2.5 Domino reductive fragmentation/ alkylation .3.2.6 Domino reductive fragmentation / olefination .3.2.7 Domino reductive fragmentation / nitromethylation .3.3 Reductive Ring Contraction .3.3.1 Ring–opening / ketyl–olefin annulation .3.3.2 Ring–opening / intramolecular carbonyl alkylation .3.4 Conclusions .References .4. Domino reactions towards carbohydrate frameworks for applications across biology and medicine Vasco Cachatra and Amélia P. Rauter .Abstract .4.1 Introduction .4.2 Domino reactions toward butenolides fused to six–membered ring sugars and thio sugars .4.3 Exploratory chemistry with amino sugars domino reactions .4.4 Domino reactions toward sugar ring contraction .  .4.4.1 Pyrano–Furano ring contraction .4.4.2 Ring contraction of furans to oxetanes .4.5 Macrocyclic bislactone synthesis via domino reaction .4.6 Sugar deoxygenation by domino reaction .4.7 Conclusion .References .5. Multistep Transformations of bis–Thioenol Ether–Containing Chiral Building Blocks: New Avenues in Glycochemistry Daniele D Alonzo, Giovanni Palumbo and Annalisa Guaragna .5.1 Introduction .5.2 (5,6–Dihydro–1,4–dithiin–2–yl)methanol: not simply a homologating agent .5.3 Sulfur–assisted multistep processes and their use in the de novo synthesis of glycostructures .5.3.1 Three steps in one process: double approach to 4–deoxy l– (and d–)–hexoses .5.3.2 Five steps in one process: the domino way to l–hexoses (and their derivatives) .5.3.3 Up to six steps in one process: 4?–substituted nucleoside synthesis .5.3.4 Eight steps in one process: beyond Achmatowicz rearrangement .5.4 Concluding remarks .Acknowledgements .References .6. Thio–click and domino approach to carbohydrate heterocycles Zbigniew J. Witczak and Roman Bielski .Abstract .6.1 Introduction .6.2 Classification and reaction mechanism .6.3 Conclusions .References      .7. Convertible Isocyanides: Application in small molecule synthesis, carbohydrate synthesis and drug discovery Soumava Santra, Tonja Andreana, Jean–Paul Bourgault and Peter R. Andreana .Abstract .7.1 Introduction .7.2 Convertible Isocyanides .7.2.1 CIC Employed in the Ugi Reaction .7.2.2 Resin–Bound Convertible Isocyanides .7.2.3 CIC Employed in the Ugi–Smile Reaction .7.2.4 CIC employed in the Joullié–Ugi Reaction .7.2.5 CIC Employed in the Passerini Reaction .7.2.6 CIC Employed in the Groebke–Blackburn–Bienayme Reaction .7.2.7 CIC Employed in the Diels–Alder Reaction .7.2.8 Monosaccharide Isocyanides Employed in the Ugi and Passerini Reaction .7.2.9 Methyl isocyanide (MIC) in the preparation of the hydroxy DKP thaxtomin .7.3 Conclusions .References .8. Adding Additional Rings to the Carbohydrate Core: Access via (Spiro) annulation Domino Processes Daniel B. Werz .Abstract .8.1 Introduction .8.2 Spiroketals via a Domino Oxidation/Rearrangement Sequence .8.3 Chromans and Isochromans via Domino Carbopalladation/ Carbopalladation/ Cyclization Sequence .References .9. Introduction to rearrangement reactions in carbohydrate chemistry Zbigniew J. Witczak and Roman Bielski .Abstract .9.1 Introduction .9.2 Classification .9.3 Chapman Rearrangement .9.4 Hofmann Rearrangement .9.5 Cope Rearrangement .9.6 Ferrier Rearrangement .9.7 Claisen Rearrangement .9.8 Overman Rearrangement .9.9 Bayer–Villiger Rearrangement .9.10 Ring Contraction .9.11 Conclusions .References .10. Rearrangement of a carbohydrate backbone discovered ?en route? to higher carbon sugars S awomir Jarosz, Anna Osuch–Kwiatkowska, Agnieszka Gajewska, and Maciej Cieplak .Abstract .10.1 Introduction .10.2 Rearrangements without changing the sugar skeleton .10.3 Rearrangements connected with the change of sugar unit(s) .10.4 Rearrangements changing the structure of a sugar skeleton .10.5 Rearrangement of the sugar skeleton discovered en route to higher carbon sugars .10.5.1 Synthesis of HCS by the Wittig type methodology .10.5.2 The acetylene/vinyltin methodology in the synthesis of HCS .10.5.3 The allyltin methodology in the synthesis of HCS .10.5.4 Rearrangement of the structure of HCS .10.5.5 Synthesis of polyhydroxylated carbocyclic derivatives with large rings. .10.6 Conclusion .Acknowledgements .References .11. Novel levoglucosenone derivatives Roman Bielski and Zbigniew J. Witczak .Abstract .11.1 Additions to the double bond of the enone system leading to the formation of new rings .11.2 Reductions of the carbonyl group followed by various reactions of the formed alcohol .11.3 Functionalization of the carbonyl group by forming carbon–nitrogen double bonds (oxymes, enamines, hydrazines) .11.4 Additions (but not cycloadditions) (particularly Michael additions) to the double bond of the enone .11.5 Enzymatic reactions of levoglucosenone .11.6 High tonnage products from levoglucosenone .11.7 Overman and allylic xanthate rearrangement .11.8 Conclusions .References .12. The preparation and reactions of 3,6–anhydro–D–glycals Vikram Basava, Emi Hanawa and Cecilia H. Marzabadi .Abstract .12.1 Introduction .12.2 Preparation of 3,6–anhydro–D–glucal under reductive conditions .12.3 Addition reactions of 3,6–anhydro–D–glucal .12.4 Preparation of 6–O–tosyl–D–galactal and reduction with lithium aluminum hydride .12.5 Conclusions .References .13. Ring Expansion Methodologies of Pyranosides to Septanosides and Structures of Septanosides Supriya Dey, N. Vijaya Ganesh and N. Jayaraman .Abstract .13.1 Introduction .13.2 Synthesis of septanosides .13.2.1 Synthesis of septanosides via hemiacetal formation .13.2.2 Knoevenagel condensation .13.2.3 Baeyer–Villiger oxidation of cyclohexanone derivatives .13.2.4 Electrophile–induced cyclization .13.2.5 Metal catalyzed cyclization .13.2.6 Nicolas–Ferrier rearrangements .13.3 Structure and conformation of septanosides .13.3.1 Solid state structures and conformations .13.3.2 Solution phase conformations .13.4 Conclusion .Acknowledgements .References .14. Rearrangements in carbohydrate templates to the way to peptide–scaffold hybrids and functionalized heterocycles Bernardo Herradón, Irene de Miguel and Enrique Mann .Abstract .14.1 Introduction .14.2 Synthesis of the chiral building blocks: applications of the Claisen–Johnson and Overman rearrangements .14.3 Peptide–scaffold hybrids .14.4 Sequential reactions for the synthesis of polyannular heterocycles .14.5 The first total synthesis of amphorogynine C .Acknowledgements .References .15. Palladium– and nickel–catalyzed stereoselective synthesis of glycosyl trichloroacetamides and their conversion to – and –urea glycosides Nathaniel H. Park, Eric T. Sletten, Matthew J. McKay, and Hien M. Nguyen .Abstract .15.1 Introduction .15.2 Development of the palladium(II)–catalyzed glycal trichloroacetimidate rearrangement .15.3 Stereoselective synthesis of glycosyl ureas from glycal trichloroacetimidates .15.4 Development of the stereoselective nickel–catalyzed transformation of glycosyl trichloroacetimidates to trichloroacetamides .15.5 Transformation of glycosyl trichloroacetimidates into – and –urea glycosides .15.6 Mechanistic studies on the nickel–catalyzed transformation of glycosyl trichloracetimidates .15.7 Conclusion .References

• ISBN: 978-1-119-04420-8
• Editorial: Wiley–Blackwell
• Encuadernacion: Cartoné
• Páginas: 368
• Fecha Publicación: 04/03/2016
• Nº Volúmenes: 1
• Idioma: Inglés