Zbigniew J. Witczak, Roman Bielski

Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience

Herausgeber: Witczak, Zbigniew J; Bielski, Roman

• Gebundenes Buch

Produktbeschreibung

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.

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Produktdetails

• Verlag: Wiley / Wiley & Sons
• Artikelnr. des Verlages: 1W119044200
• 1. Auflage
• Seitenzahl: 368
• Erscheinungstermin: 23. Februar 2016
• Englisch
• Abmessung: 240mm x 161mm x 25mm
• Gewicht: 724g
• ISBN-13: 9781119044208
• ISBN-10: 1119044200
• Artikelnr.: 42953618

Autorenporträt

Zbigniew J. Witczak obtained his Ph.D. from Medical University of Lodz, Faculty of Pharmacy (Poland). After postdoctoral work at Purdue University, he worked in industry (A. E.Staley), then joined the faculty of the School of Pharmacy at University of Connecticut. He moved to Wilkes University, Nesbitt School of Pharmacy in 2000, where he is Full Professor. He has published over ninety research papers and holds six patents in the fields of carbohydrate medicinal and biological chemistry. In 2000 he was awarded the Melville L. Wolfrom Award of the ACS Division of Carbohydrate Chemistry. His research interests are in the area of carbohydrate Synthons including Levoglucosenone and L-Arabinose as template for carbohydrate based therapeutics. Roman Bielski obtained his Ph.D. at the Institute of Organic Chemistry, Polish Academy of Sciences. He is currently a Senior Scientist in Value Recovery, Inc., a partner in Cheminnolab, LLC, and adjunct professor at Wilkes University. Recently he (with M. Tencer) developed a method of enantiomers' resolution requiring no use of chiral compounds. His research interests are origin of homochirality, modification of carbohydrates, solutions to environmental issues and sustainability. He published over three dozen papers and co-authored 18 patents.

Inhaltsangabe

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-