Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience
1. Auflage April 2016
368 Seiten, Hardcover
Wiley & Sons Ltd
ISBN:
978-1-119-04420-8
John Wiley & Sons
The book consists of a brief introduction, a foreward provided by professor Danishefsky of Columbia University, and about 14 - 16 chapters, each written by one or two eminent scholars/authors describing their recent research in the area of either domino reactions or intramolecular rearrangements in carbohydrate chemistry. Three or
four chapters will be reviews. The domino (cascade, tandem) reactions are always intramolecular. They are usually very fast, clean and offer highly complex structures in a one pot process. Intramolecular rearrangements offer very similar advantages and often lead to highly complex products as well. Although many recently isolated carbohydrates fulfill various sophisticated functions, their structures are often very complex. The editors cover the broadest scope of novel methodologies possible. All the synthetic and application aspects of domino/cascade reactions are explored in this book. A second theme that will be covered is intramolecular rearrangement, which is also fast, stereoselective, and often constitutes one or more steps of domino /cascade process. Selected examples of intramolecular rearrangements are presented. Together, both processes offer an elegant and
convenient approach to the synthesis of many complex molecules, which are normally difficult to synthesize via alternative routes. It appears that domino and intramolecular rearrangements are ideally suited to synthesize certain specific modified monosaccharides. What is particularly important is that both processes are intermolecular and almost always yield products with very well-defined stereochemistry. This high definition is absolutely crucial when synthesizing advanced, modified mono and oligosaccharides. The choice of contributors reflects an emphasis
on both therapeutic and pharmacological aspects of carbohydrate chemistry.
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
SBawomir 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 alpha- and beta-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 alpha- and beta-urea glycosides
15.6 Mechanistic studies on the nickel-catalyzed transformation of glycosyl trichloracetimidates
15.7 Conclusion
References
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
SBawomir 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 alpha- and beta-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 alpha- and beta-urea glycosides
15.6 Mechanistic studies on the nickel-catalyzed transformation of glycosyl trichloracetimidates
15.7 Conclusion
References
