Efficiency in Natural Product Total Synthesis

1. Auflage 2018
ISBN: 978-1-118-60540-0
Verlag: John Wiley & Sons

Buch, Englisch, 512 Seiten, Format (B × H): 157 mm x 235 mm, Gewicht: 887 g

Uniting the key organic topics of total synthesis and efficient synthetic methodologies, this book clearly overviews synthetic strategies and tactics applied in total synthesis, demonstrating how the total synthesis of natural products enables scientific and drug discovery.

• Focuses on efficiency, a fundamental and important issue in natural products synthesis that makes natural product synthesis a powerful tool in biological and pharmaceutical science
• Describes new methods like organocatalysis, multicomponent and cascade reactions, and biomimetic synthesis
• Appeals to graduate students with two sections at the end of each chapter illustrating key reactions, strategies, tactics, and concepts; and good but unfinished total synthesis (synthesis of core structure) before the last section
• Compiles examples of solid phase synthesis and continuing flow chemistry-based total synthesis which are very relevant and attractive to industry R&D professionals

Autoren/Hrsg.

Huang, Pei-Qiang

Yao, Zhu-Jun

Hsung, Richard P.

Weitere Mitwirkende

Wong, Henry N.C.

Fachgebiete

• Naturwissenschaften Chemie Chemie Allgemein Pharmazeutische Chemie, Medizinische Chemie
• Naturwissenschaften Chemie Organische Chemie

Inhaltsverzeichnis

Contributors xiii

Foreword xv

Preface xvii

Introduction 1
Pei-Qiang Huang

1 The Golden Age of the Total Synthesis of Natural Products: The Era as a Dominant Field 2

2 1991–2000: A Contrasting Decade 9

3 Total Synthesis in the Twenty-First Century 10

4 The Challenges of the Efficiency in the Total Synthesis of Natural Products 12

5 The Renaissance of Natural Products as Drug Candidates 14

6 Recent Recognition of the Contribution of Natural Product-Based Drugs to Society 16

Acknowledgements 18

References 18

1 Principles for Synthetic Efficiency and Expansion of the Field 27
Pei-Qiang Huang

1.1 Concepts for Efficiency in the Total Synthesis of Natural Products 27

1.1.1 Ideal Synthesis 28

1.1.2 Selectivity 29

1.1.3 Green Synthesis 32

1.1.4 Atom Economy 32

1.1.5 E Factors 32

1.1.6 Step Economy 33

1.1.7 Pot Economy and PASE (Pot, Atom, and Step Economy) 34

1.1.8 Redox Economy 34

1.1.9 Protecting-Group-Free Synthesis 36

1.1.10 Multicomponent Reactions and One-Pot Reactions 38

1.1.11 Scalability 40

1.1.12 Convergent Synthesis 41

1.2 Biomimetic Synthesis 41

1.2.1 Basic Logic of Biosynthesis 42

1.2.2 Tandem, Cascade, and Domino Reactions – One-Pot Reactions 42

1.2.3 Site and Stereoselective Reactions 46

1.2.4 The C-H Bond Functionalization Strategy 46

1.2.5 The Building-Block Strategy 47

1.2.6 The Collective Synthesis Strategy 49

1.2.7 The Oligomerization Tactic 50

1.3 The Expansion of the Field: Chemical Biology/Chemical Genetics 51

1.3.1 Diversity-Oriented Synthesis (DOS) 51

1.3.2 Function-Oriented Synthesis (FOS) 51

1.3.3 Biology-Oriented Synthesis (BIOS) 52

1.3.4 Lead-Oriented Synthesis (LOS) 52

1.4 Addressing the Threats that Humans May Face in the Near Future 53

1.4.1 A. G. Myers’ Endeavor 53

1.4.2 D.

Über Autor(innen)

Pei-Qiang Huang, PhD, is Professor of Chemistry and former Dean of the College of Chemistry and Chemical Engineering at Xiamen University.

Zhu-Jun Yao, PhD, is Cyrus Tang Chair Professor and University Distinguished Professor at Nanjing University.

Richard P. Hsung, PhD, is Kremers Chair and Vials Distinguished Professor of Pharmaceutical Sciences at School of Pharmacy, University of Wisconsin-Madison.