From Biosynthesis to Total Synthesis

Strategies and Tactics for Natural Products
1. Auflage 2016
ISBN: 978-1-118-75173-2
Verlag: Wiley

Buch, Englisch, 584 Seiten, Format (B × H): 220 mm x 287 mm, Gewicht: 1575 g

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

Autoren/Hrsg.

Zografos, Alexandros L

Fachgebiete

• Naturwissenschaften Chemie Organische Chemie Biochemie

Inhaltsverzeichnis

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

Über Autor(innen)

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.