Alexandros L. Zografos

From Biosynthesis to Total Synthesis (eBook, PDF)

Strategies and Tactics for Natural Products

• Format: PDF

Produktbeschreibung

Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis. By discussing major biosynthetic pathways and their chemical reactions, transformations, and natural products applications; it links biosynthetic mechanisms and more efficient total synthesis. * Describes four major biosynthetic pathways (acetate, mevalonate, shikimic acid, and mixed pathways and alkaloids) and their related mechanisms * Covers reactions, tactics, and strategies for chemical transformations, linking biosynthetic processes and total synthesis * Includes strategies for optimal synthetic plans and introduces a modern molecular approach to natural product synthesis and applications * Acts as a key reference for industry and academic readers looking to advance knowledge in classical total synthesis, organic synthesis, and future directions in the field

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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 584
• Erscheinungstermin: 17. März 2016
• Englisch
• ISBN-13: 9781118753569
• Artikelnr.: 44870692

Autorenporträt

Alexandros L. Zografos graduated as a chemist from the National and Kapodistrian University of Athens, Greece. After earning his PhD in 2001 at the National Technical University of Athens, he pursued his postdoctoral studies with Prof. Phil Baran at the Scripps Research Institute and Prof. Scott Snyder at Columbia University before he moved back to Greece to work as a senior researcher at the National and Kapodistrian University of Athens and NCRS Demokritos Institute. In 2009, he began his independent career at the Aristotle University of Thessaloniki, Greece, where he is currently an assistant professor of organic chemistry. His group is working on divergent total synthesis of complex natural products and on the development of novel CH activation reactions.

Inhaltsangabe

LIST OF CONTRIBUTORS xiii

PREFACE xv

1 From Biosyntheses to Total Syntheses: An Introduction 1
Bastien Nay and Xu-Wen Li

1.1 From Primary to Secondary Metabolism: the Key Building Blocks 1

1.1.1 Definitions 1

1.1.2 Energy Supply and Carbon Storing at the Early Stage of Metabolisms 1

1.1.3 Glucose as a Starting Material Toward Key Building Blocks of the Secondary Metabolism 1

1.1.4 Reactions Involved in the Construction of Secondary Metabolites 3

1.1.5 Secondary Metabolisms 4

1.2 From Biosynthesis to Total Synthesis: Strategies Toward the Natural Product Chemical Space 10

1.2.1 The Chemical Space of Natural Products 10

1.2.2 The Biosynthetic Pathways as an Inspiration for Synthetic Challenges 11

1.2.3 The Science of Total Synthesis 14

1.2.4 Conclusion: a Journey in the Future of Total Synthesis 16

References 16

SECTION I ACETATE BIOSYNTHETIC PATHWAY 19

2 Polyketides 21
Françoise Schaefers, Tobias A. M. Gulder, Cyril Bressy, Michael Smietana, Erica Benedetti, Stellios Arseniyadis, Markus Kalesse, and Martin Cordes

2.1 Polyketide Biosynthesis 21

2.1.1 Introduction 21

2.1.2 Assembly of Acetate/Malonate-Derived Metabolites 23

2.1.3 Classification of Polyketide Biosynthetic Machineries 23

2.1.4 Conclusion 39

References 40

2.2 Synthesis of Polyketides 44

2.2.1 Asymmetric Alkylation Reactions 44

2.2.2 Applications of Asymmetric Alkylation Reactions in Total Synthesis of Polyketides and Macrolides 60

References 83

2.3 Synthesis of Polyketides-Focus on Macrolides 87

2.3.1 Introduction 87

2.3.2 Stereoselective Synthesis of 1,3-Diols: Asymmetric Aldol Reactions 88

2.3.3 Stereoselective Synthesis of 1,3-Diols: Asymmetric Reductions 106

2.3.4 Application of Stereoselective Synthesis of 1,3-Diols in the Total Synthesis of Macrolides 117

2.3.5 Conclusion 126

References 126

3 Fatty Acids and their Derivatives 130
Anders Vik and Trond Vidar Hansen

3.1 Introduction 130

3.2 Biosynthesis 130

3.2.1 Fatty Acids and Lipids 130

3.2.2 Polyunsaturated Fatty Acids 134

3.2.3 Mediated Oxidations of omega-3 and omega-6 Polyunsaturated Fatty Acids 135

3.3 Synthesis of omega-3 and omega-6 All-Z Polyunsaturated Fatty Acids 140

3.3.1 Synthesis of Polyunsaturated Fatty Acids by the Wittig Reaction or by the Polyyne Semihydrogenation 140

3.3.2 Synthesis of Polyunsaturated Fatty Acids via Cross Coupling Reactions 143

3.4 A pplications in Total Synthesis of Polyunsaturated Fatty Acids 145

3.4.1 Palladium-Catalyzed Cross Coupling Reactions 145

3.4.2 Biomimetic Transformations of Polyunsaturated Fatty Acids 149

3.4.3 Landmark Total Syntheses 153

3.4.4 Synthesis of Leukotriene B5 158

3.5 Conclusion 160

Acknowledgments 160

References 160

4 Polyethers 162
Youwei Xie and Paul E. Floreancig

4.1 Introduction 162

4.2 Biosynthesis 162

4.2.1 Ionophore Antibiotics 162

4.2.2 Marine Ladder Toxins 165

4.2.3 A nnonaceous Acetogenins and Terpene Polyethers 165

4.3 Epoxide Reactivity and Stereoselective Synthesis 166

4.3.1 Regiocontrol in Epoxide-Opening Reactions 166

4.3.2 Stereoselective Epoxide Synthesis 172

4.4 A pplications to Total Synthesis 176

4.4.1 Acid-Mediated Transformations 176

4.4.2 Cascades via Epoxonium Ion Formation 179

4.4.3 Cyclizations under Basic