Includes bibliographical references and index.

Foreword Stuart L. Schreiber Preface List of Contributors Abbreviations 1 The Basics of Diversity-Oriented Synthesis Kieron M. G. O'Connell, Warren R. J. D. Galloway and David R. Spring 1.1 Introduction 1.2 What is Diversity-Oriented Synthesis? 1.3 Small Molecules and Biology 1.4 Comparing DOS, TOS and Combinatorial Chemistry (Focused Library Synthesis) 1.5 Molecular Diversity 1.6 Molecular Diversity and Chemical Space 1.7 Synthetic Strategies for Creating Molecular Diversity 1.8 Reagent-Based Approaches to Diversity Generation 1.9 A Substrate-Based Approach to Skeletal Diversity Generation 1.10 Other Build/Couple/Pair Examples 1.11 Concluding Remarks 1.12 References Part I Chemical Methodology in Diversity-Oriented Synthesis 2 Strategies Applications of Multicomponent Reactions (MCRs) to Diversity-Oriented Synthesis John M. Knapp, Mark J. Kurth, Jared T. Shaw and Ashkaan Younai 2.1 Introduction 2.2 MCR Products for HTS 2.3 MCRs as Starting Points for DOS 2.4 Conclusion 2.5 References 3 Cycloaddition Reactions in Diversity-Oriented Synthesis Giovanni Muncipinto 3.1 Introduction 3.2 [4+2] Cycloaddition Reactions 3.3 Diels-Alder Reaction 3.4 Inverse Electron Demand Diels-Alder Reaction 3.5 1,3-dipolar Cycloaddition Reactions 3.6 Miscellaneous Cycloadditions 3.7 Conclusion 3.8 References 4 Phosphine Organocatalysis as the Platform for Diversity-Oriented Synthesis Ohyun Kwon and Zhiming Wang 4.1 Introduction 4.2 DOS using Phosphine Organocatalysis 4.2.1 Phosphine Organocatalysis of Allenes with Imines 4.3 Skeletal Diversity Based on a Phosphine Catalysis/Combinatorial Scaffolding Strategy 4.4 A DOS Library Based on Phosphine Organocatalysis: Biological Screening, Analogue Synthesis, and Structure--Activity Relationship Analysis 4.5 Conclusions 4.6 References 5 Domino Reactions in Library Synthesis Matthew G. LaPorte, John R. Goodell, Sammi Tsegay and Peter Wipf 5.1 Introduction 5.2 Pericyclic Domino Reactions 5.3 Anionic Domino Reactions 5.4 Transition Metal Mediated Domino Reactions 5.5 Radical Domino Reactions 5.6 Conclusions 5.7 References 6 Diversity-Oriented Synthesis of Amino Acid-Derived Scaffolds and Peptidomimetics: A Perspective Andrea Trabocchi 6.1 Introduction 6.2 Definition and Classification of Peptidomimetics 6.3 Early Combinatorial Approaches to Peptidomimetic Scaffolds 6.4 Amino Acid-Derived Scaffolds 6.5 Macrocyclic Peptidomimetic Scaffolds 6.6 Conclusion 6.7 References 7 Solid-phase Synthesis Enabling Chemical Diversity Viktor Krchnak and Nade da Cankarova 7.1 Introduction 7.2 Skeletal Diversity 7.3 Substrate-Based Strategy (Folding Process) 7.4 Stereochemical Diversity 7.5 Appendages Diversity 7.6 Build/Couple/Pair Strategy 7.7 Scaffold Hopping 7.8 Conclusion 7.9 References 8 Macrocycles as Templates for Diversity Generation in Drug Discovery Eric Marsault 8.1 Introduction 8.2 Challenges Associated with Macrocycles 8.3 Macrocyclic Peptides 8.4 Peptidomimetic Macrocycles 8.5 Diversity-Oriented Strategies Based on Nonpeptidic Natural Products 8.6 Conclusion 8.7 References Part II Chemical Libraries and Diversity-Oriented Synthesis 9 Diversity-Oriented Synthesis of Natural Product-Based Libraries Mark Dow, Francesco Marchetti and Adam Nelson 9.1 Introduction 9.2 Libraries Inspired by Natural Product Scaffolds 9.3 Folding Pathways in the Synthesis of Natural Product-Like Libraries 9.4 Branching Pathways in the Synthesis of Natural Product-Like Libraries 9.5 Oligomer-Based Approaches to Natural Product-Like Libraries 9.6 Summary 9.7 References 10 Chemoinformatic Characterization of the Chemical Space and Molecular Diversity of Compound Libraries Jose Luis Medina-Franco 10.1 Introduction 10.2 Concept of Chemical Space 10.3 General Aspects of Chemoinformatic Methods to Analyze the Chemical Space 10.4 Chemoinformatic-Based Analysis of Libraries Using Different Representations 10.5 Rec