Efficiency in natural products total synthesis. (2016)

• Record Type: Book
• Further Information: Note: Pei-Qiang Huang, Zhu-Jun Yao, Richard Hsung.
• Authors: Huang, Pei-Qiang; Yao, Zhu-Jun; Hsung, Richard
• Contents: 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„ŸH 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. L. Boger’s Endeavor 55 Acknowledgements 56 References 56 2 Selected Procedure?-Economical Enantioselective Total Syntheses of Natural Products 67; Pei?-Qiang Huang 2.1 One?-Step/One?-Pot Enantioselective Total Synthesis of Natural Products/Drugs 68 2.1.1 Robinson’s One?-Step Synthesis of Tropinone 68 2.1.2 Hayashi’s One?-Pot Synthesis of (+)?-ABT?-341 69 2.2 Two?-Step/Two?-Pot Enantioselective Total Synthesis of Natural Products 69 2.2.1 Hayashi’s Two?-Pot Synthesis of (−)?-Oseltamivir 69 2.2.2 Ma’s Two?-Pot Synthesis of (−)?-Oseltamivir 70 2.2.3 Li’s Two?-Step Chemoenzymatic Total Synthesis of Aszonalenin 71 2.2.4 Ishikawa’s Two?-Step Total Syntheses of (+)?-WIN 64821 and (+)?-Naseseazine B 71 2.3 Three?-Step/Three?-Pot Enantioselective Total Synthesis of Natural Products 73 2.3.1 Carreira’s Three?-Step Asymmetric Total Syntheses of (+)?-Aszonalenin and (−)?-Brevicompanine B 73 2.3.2 Husson’s Three?-Step Asymmetric Total Synthesis of (−)?-Sibirine 73 2.3.3 MacMillan’s Three?-Step Asymmetric Total Synthesis of (+)?-Frondosin B 75 2.3.4 Hayashi’s Three?-Pot Total Synthesis of (−)?-PGE1 Methyl Ester 75 2.3.5 Porco’s Three?-Pot Total Synthesis of (−)?-Hyperibone K 76 2.4 Four?-Step Enantioselective Total Synthesis of Natural Products 77 2.4.1 Lawrence’s Four?-Step Total Synthesis of (−)?-Angiopterlactone A 77 2.4.2 Maimone’s Four?-Step Synthesis of (+)?-Cardamom Peroxide 78 2.4.3 Xie, Lai, and Ma’s Four?-Step Total Synthesis of (−)?-Chimonanthine 79 2.4.4 Huang’s Four?-Step Total Synthesis of (−)?-Chaetominine 80 2.5 Five?-Step/Pot Enantioselective Total Synthesis of Natural Products 81 2.5.1 Carreira’s Five?-Step Total Syntheses of Δ9?-Tetrahydrocannabinols 81 2.5.2 Studer’s Five?-Step Total Syntheses of (+)?-Machaeriols B and D 83 2.5.3 Cook’s Five?-Pot Total Synthesis of (+)?-Artemisinin (Qinghaosu) 84 2.5.4 Corey’s Five?-Step Total Synthesis of Aflatoxin B2 85 2.6 Six?-Step Enantioselective Total Synthesis of Natural Products 86 2.6.1 Comins’ Six?-Step Total Synthesis of (S)?-Camptothecin 86 2.6.2 Krische’s Six?-Step Total Synthesis of (−)?-Cyanolide A 87 2.7 Seven?-Step Enantioselective Total Synthesis of Natural Products 89 2.7.1 Baran’s 7–10?-Step Total Syntheses of Hapalindole?-Type Natural Products 89 2.7.2 Aggarwal’s Seven?-Step Total Synthesis of (+)?-PGF2α 90 2.7.3 Echavarren’s Seven?-step Total Syntheses of Aromadendrane Sesquiterpenes 93 2.7.4 Zhu’s Seven?-Step Total Synthesis of Peganumine A 94 2.7.5 Rychnovsky’s Seven?-Step Synthesis of Lycopodium Alkaloid (+)?-Fastigiatine 96 2.8 Eight?-Step Enantioselective Total Synthesis of Natural Products 99 2.8.1 Overman’s Eight?-Step Synthesis of (+)?-Trans?-Clerodane Iterpenoid 99 2.8.2 Chain’s Eight?-Step Synthesis of (−)?-Englerin A 100 2.8.3 Shenvi’s Eight?-Step Total Synthesis of (−)?-Jiadifenolide 102 2.8.4 Maimone’s Eight?-Step Total Synthesis of (+)?-Chatancin 103 2.8.5 Wipf’s Eight?-Step Total Synthesis of (−)?-Cycloclavine 105 2.8.6 Shenvi’s Eight?-Step Total Synthesis of (−)?- Neothiobinupharidine 108 2.9 Nine?-Step Enantioselective Total Synthesis of Natural Products 110 2.9.1 Stoltz’s Nine?-Step Total Synthesis of (−)?-Cyanthiwigin F 110 2.9.2 Maimone’s Nine?-Step Total Synthesis of (–)?-6?-Epi-Ophiobolin N 112 2.9.3 MacMillan’s Nine?-Step Total Synthesis of (−)?-Vincorine 114 2.9.4 Ramharter’s Nine?-Step Total Synthesis of (+)?-Lycoflexine 116 2.9.5 Gao’s and Theodorakis’ Nine?-Step Total Syntheses of (+)?-Fusarisetin A 118 2.10 Ten/Eleven?-Step Enantioselective Total Syntheses of Natural Products 121 2.10.1 Lin’s 10?-Step Total Synthesis of (−)?-Huperzine A 121 2.10.2 Trauner’s 10?-Step Total Synthesis of (+)?-Loline 122 2.10.3 Zhai’s 10?-Step Total Synthesis of (+)?-Absinthin 124 2.10.4 Baran’s 11?-Step Total Synthesis of (−)?-Maoecrystal V 125 2.11 Fourteen/Fifteen?-Step Enantioselective Total Synthesis of Natural Products 129 2.11.1 Baran’s 14?-Step Total Synthesis of (−)?-Ingenol 129 2.11.2 Reisman’s 15?-Step Total Synthesis of (+)?-Ryanodol 132 2.11.3 Johnson’s 15?-Step Total Synthesis of (+)?-Pactamycin 134 2.12 Other Procedure?-Economical Enantioselective Total Syntheses of Natural Products 137 2.13 Conclusion 137 Acknowledgements 149 References 149 3 Diels–Alder Cascades in Natural Product Total Synthesis 159; Richard P. Hsung, Zhi?-Xiong Ma, Lichao Fang, and John B. Feltenberger 3.1 Introduction 159 3.2 Cascades Initiated by Coupling of a Pre?-Formed Diene and Dienophile 161 3.3 Simple Transformations to Diene/Dienophiles Followed by the Diels–Alder Cascade 163 3.4 Rearrangement?-Initiated Diels–Alder Cascades 170 3.5 Cyclization?-Initiated Diels–Alder Cascades 175 3.6 Diels–Alder Initiated Cascades 180 3.7 Concluding Remarks 185 Acknowledgements 185 References 185 4 Organometallics?-Based Catalytic (Asymmetric) Synthesis of Natural Products 191; Hongbin Zhai, Yun Li, Bin Cheng, Zhiqiang Ma, Peng Gao, Xin Chen, Weihe Zhang, Hanwei Hu, and Fang Fang 4.1 Introduction 191 4.2 Au?-Catalyzed Reactions in Total Synthesis 191 4.3 Ag?-Catalyzed Reactions in Total Synthesis 195 4.4 Pt?-Catalyzed Reactions in Total Synthesis 199 4.4.1 Pt?-Catalyzed Enyne Cycloisomerization Reactions 199 4.5 Co?-Catalyzed Pauson–Khand Reactions and Hetero?-Pauson–Khand Reactions in Total Synthesis 202 4.6 Cu?-Catalyzed Reactions in Total Synthesis 204 4.6.1 Asymmetric Conjugate Addition 205 4.6.2 Arene Cyclopropanation 208 4.7 Chromium?-Catalyzed Reactions in Total Synthesis 209 4.8 Fe?-Mediated
• Edition: 1st
• Publisher Details: Hoboken, New Jersey : John Wiley & Sons, Inc
• Publication Date: 2016
• Extent: 1 online resource
• Subjects: 547.2; Organic compounds -- Synthesis; Natural products -- Synthesis
• Languages: English
• ISBNs: 9781118940211
• Related ISBNs: 9781118940204
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