Efficiency in Natural Product Total Synthesis.

Intro -- Title Page -- Copyright Page -- Contents -- Contributors -- Foreword -- Preface -- Introduction -- 1 The Golden Age of the Total Synthesis of Natural Products: The Era as a Dominant Field -- 2 1991-2000: A Contrasting Decade -- 3 Total Synthesis in the Twenty‐First Century -- 4 The Challenges of the Efficiency in the Total Synthesis of Natural Products -- 5 The Renaissance of Natural Products as Drug Candidates -- 6 Recent Recognition of the Contribution of Natural Product-Based Drugs to Society -- Acknowledgements -- References -- Chapter 1 Principles for Synthetic Efficiency and Expansion of the Field -- 1.1 Concepts for Efficiency in the Total Synthesis of Natural Products -- 1.1.1 Ideal Synthesis -- 1.1.2 Selectivity -- 1.1.3 Green Synthesis -- 1.1.4 Atom Economy -- 1.1.5 E Factors -- 1.1.6 Step Economy -- 1.1.7 Pot Economy and PASE (Pot, Atom, and Step Economy) -- 1.1.8 Redox Economy -- 1.1.9 Protecting-Group-Free Synthesis -- 1.1.10 Multicomponent Reactions and One-Pot Reactions -- 1.1.11 Scalability -- 1.1.12 Convergent Synthesis -- 1.2 Biomimetic Synthesis -- 1.2.1 Basic Logic of Biosynthesis -- 1.2.2 Tandem, Cascade, and Domino Reactions - One-Pot Reactions -- 1.2.3 Site and Stereoselective Reactions -- 1.2.4 The C─H Bond Functionalization Strategy -- 1.2.5 The Building-Block Strategy -- 1.2.6 The Collective Synthesis Strategy -- 1.2.7 The Oligomerization Tactic -- 1.3 The Expansion of the Field: Chemical Biology/Chemical Genetics -- 1.3.1 Diversity-Oriented Synthesis (DOS) -- 1.3.2 Function-Oriented Synthesis (FOS) -- 1.3.3 Biology-Oriented Synthesis (BIOS) -- 1.3.4 Lead-Oriented Synthesis (LOS) -- 1.4 Addressing the Threats that Humans May Face in the Near Future -- 1.4.1 A. G. Myers' Endeavor -- 1.4.2 D. L. Boger's Endeavor -- Acknowledgements -- References.

Chapter 2 Selected Procedure-Economical Enantioselective Total Syntheses of Natural Products -- 2.1 One-Step/One-Pot Enantioselective Total Synthesis of Natural Products/Drugs -- 2.1.1 Robinson's One-Step Synthesis of Tropinone -- 2.1.2 Hayashi's One-Pot Synthesis of (+)-ABT-341 -- 2.2 Two-Step/Two-Pot Enantioselective Total Synthesis of Natural Products -- 2.2.1 Hayashi's Two-Pot Synthesis of (−)-Oseltamivir -- 2.2.2 Ma's Two-Pot Synthesis of (−)-Oseltamivir -- 2.2.3 Li's Two-Step Chemoenzymatic Total Synthesis of Aszonalenin -- 2.2.4 Ishikawa's Two-Step Total Syntheses of (+)-WIN 64821 and (+)-Naseseazine B -- 2.3 Three-Step/Three-Pot Enantioselective Total Synthesis of Natural Products -- 2.3.1 Carreira's Three-Step Asymmetric Total Syntheses of (+)-Aszonalenin and (−)-Brevicompanine B -- 2.3.2 Husson's Three-Step Asymmetric Total Synthesis of (−)-Sibirine -- 2.3.3 MacMillan's Three-Step Asymmetric Total Synthesis of (+)-Frondosin B -- 2.3.4 Hayashi's Three-Pot Total Synthesis of (−)-PGE1 Methyl Ester -- 2.3.5 Porco's Three-Pot Total Synthesis of (−)-Hyperibone K -- 2.4 Four-Step Enantioselective Total Synthesis of Natural Products -- 2.4.1 Lawrence's Four-Step Total Synthesis of (−)-Angiopterlactone A -- 2.4.2 Maimone's Four-Step Synthesis of (+)-Cardamom Peroxide -- 2.4.3 Xie, Lai, and Ma's Four-Step Total Synthesis of (−)-Chimonanthine -- 2.4.4 Huang's Four-Step Total Synthesis of (−)-Chaetominine -- 2.5 Five-Step/Pot Enantioselective Total Synthesis of Natural Products -- 2.5.1 Carreira's Five-Step Total Syntheses of Δ9-Tetrahydrocannabinols -- 2.5.2 Studer's Five-Step Total Syntheses of (+)-Machaeriols B and D -- 2.5.3 Cook's Five-Pot Total Synthesis of (+)-Artemisinin (Qinghaosu) -- 2.5.4 Corey's Five-Step Total Synthesis of Aflatoxin B2 -- 2.6 Six-Step Enantioselective Total Synthesis of Natural Products.

2.6.1 Comins' Six-Step Total Synthesis of (S)-Camptothecin -- 2.6.2 Krische's Six-Step Total Synthesis of (−)-Cyanolide A -- 2.7 Seven-Step Enantioselective Total Synthesis of Natural Products -- 2.7.1 Baran's 7-10-Step Total Syntheses of Hapalindole-Type Natural Products -- 2.7.2 Aggarwal's Seven-Step Total Synthesis of (+)-PGF2α -- 2.7.3 Echavarren's Seven-step Total Syntheses of Aromadendrane Sesquiterpenes -- 2.7.4 Zhu's Seven-Step Total Synthesis of Peganumine A -- 2.7.5 Rychnovsky's Seven-Step Synthesis of Lycopodium Alkaloid (+)-Fastigiatine -- 2.8 Eight-Step Enantioselective Total Synthesis of Natural Products -- 2.8.1 Overman's Eight-Step Synthesis of (+)-Trans-Clerodane Iterpenoid -- 2.8.2 Chain's Eight-Step Synthesis of (−)-Englerin A -- 2.8.3 Shenvi's Eight-Step Total Synthesis of (−)-Jiadifenolide -- 2.8.4 Maimone's Eight-Step Total Synthesis of (+)-Chatancin -- 2.8.5 Wipf's Eight-Step Total Synthesis of (−)-Cycloclavine -- 2.8.6 Shenvi's Eight-Step Total Synthesis of (−)-Neothiobinupharidine -- 2.9 Nine-Step Enantioselective Total Synthesis of Natural Products -- 2.9.1 Stoltz's Nine-Step Total Synthesis of (−)-Cyanthiwigin F -- 2.9.2 Maimone's Nine-Step Total Synthesis of (-)-6‐Epi-Ophiobolin N -- 2.9.3 MacMillan's Nine-Step Total Synthesis of (−)-Vincorine -- 2.9.4 Ramharter's Nine-Step Total Synthesis of (+)-Lycoflexine -- 2.9.5 Gao's and Theodorakis' Nine-Step Total Syntheses of (+)-Fusarisetin A -- 2.10 Ten/Eleven-Step Enantioselective Total Syntheses of Natural Products -- 2.10.1 Lin's 10-Step Total Synthesis of (−)-Huperzine A -- 2.10.2 Trauner's 10-Step Total Synthesis of (+)-Loline -- 2.10.3 Zhai's 10-Step Total Synthesis of (+)-Absinthin -- 2.10.4 Baran's 11-Step Total Synthesis of (−)-Maoecrystal V -- 2.11 Fourteen/Fifteen-Step Enantioselective Total Synthesis of Natural Products.

2.11.1 Baran's 14-Step Total Synthesis of (−)-Ingenol -- 2.11.2 Reisman's 15-Step Total Synthesis of (+)-Ryanodol -- 2.11.3 Johnson's 15-Step Total Synthesis of (+)-Pactamycin -- 2.12 Other Procedure-Economical Enantioselective Total Syntheses of Natural Products -- 2.13 Conclusion -- Acknowledgements -- References -- Chapter 3 Diels-Alder Cascades in Natural Product Total Synthesis -- 3.1 Introduction -- 3.2 Cascades Initiated by Coupling of a Pre-Formed Diene and Dienophile -- 3.3 Simple Transformations to Diene/Dienophiles Followed by the Diels-Alder Cascade -- 3.4 Rearrangement-Initiated Diels-Alder Cascades -- 3.5 Cyclization-Initiated Diels-Alder Cascades -- 3.6 Diels-Alder Initiated Cascades -- 3.7 Concluding Remarks -- Acknowledgements -- References -- Chapter 4 Organometallics-Based Catalytic (Asymmetric) Synthesis of Natural Products -- 4.1 Introduction -- 4.2 Au-Catalyzed Reactions in Total Synthesis -- 4.3 Ag-Catalyzed Reactions in Total Synthesis -- 4.4 Pt-Catalyzed Reactions in Total Synthesis -- 4.4.1 Pt-Catalyzed Enyne Cycloisomerization Reactions -- 4.5 Co-Catalyzed Pauson-Khand Reactions and Hetero-Pauson-Khand Reactions in Total Synthesis -- 4.6 Cu-Catalyzed Reactions in Total Synthesis -- 4.6.1 Asymmetric Conjugate Addition -- 4.6.2 Arene Cyclopropanation -- 4.7 Chromium-Catalyzed Reactions in Total Synthesis -- 4.8 Fe-Mediated Coupling Reactions in Total Synthesis -- 4.8.1 Reaction with Acid Chlorides -- 4.8.2 Reaction with Alkenyl Electophiles -- 4.8.3 Reaction with Aryl Halides -- 4.8.4 Reaction with Alkyl Halides -- 4.8.5 Related Iron-Catalyzed C-C Bond Formations -- 4.8.6 Iron-Catalyzed C-O, C-S, and C-N Cross-Coupling -- 4.9 Mn-Mediated Coupling Reactions in Total Synthesis -- 4.10 Ni-Catalyzed Reactions in Total Synthesis -- 4.10.1 Ni-Catalyzed Cycloadditions -- 4.10.2 Ni-Catalyzed Coupling Reactions.

4.11 Pd-Catalyzed Cross-Coupling Reactions in Total Synthesis -- 4.11.1 Heck Reactions in Total Synthesis -- 4.11.2 Suzuki Reactions in Total Synthesis -- 4.11.3 Stille Reactions in Total Synthesis -- 4.11.4 Tsuji-Trost Reactions in Total Synthesis -- 4.11.5 Negishi Reactions in Total Synthesis -- 4.11.6 Pd-Catalyzed Domino Reactions in Total Synthesis -- 4.12 Rh-Catalyzed (C-H Functionalization by Metal Carbenoid and Nitrenoid Insertion) Reactions in Total Synthesis -- 4.13 Ru-Catalyzed RCM  and RCAM  in Total Synthesis -- 4.14 Conclusion -- Acknowledgements -- References -- Chapter 5 C-H Activation-Based Strategy for Natural Product Synthesis -- 5.1 Introduction -- 5.2 Recently Completed Total Syntheses of Natural Products via a C-H Activation Approach -- 5.3 Conclusion -- Acknowledgements -- References -- Chapter 6 Recent Applications of Kagan's Reagent (SmI2) in Natural Product Synthesis -- 6.1 Background -- 6.1.1 The Reformatsky Reaction -- 6.1.2 Carbonyl/Alkene Reductive Reactions -- 6.1.3 Pinacol-Type Couplings -- 6.1.4 Fragmentation Reactions -- 6.2 SmI2-Mediated Reactions in Natural Product Synthesis -- 6.2.1 Synthesis of (+)-Acutiphycin -- 6.2.2 Synthesis of Brevetoxin B -- 6.2.3 Synthesis of (±)-Vigulariol -- 6.2.4 Synthesis of Diazonamide A -- 6.2.5 Synthesis of Epothilone A -- 6.2.6 Synthesis of Strychnine -- 6.2.7 Synthesis of the ABC Ring of Paclitaxel -- 6.2.8 Miscellaneous -- 6.3 Conclusion -- Acknowledgements -- References -- Chapter 7 Asymmetric Organocatalysis in the Total Synthesis of Complex Natural Products -- 7.1 Background -- 7.2 Total Synthesis of Alkaloids -- 7.2.1 Synthesis of (−)-Flustramine B -- 7.2.2 Enantioselective Total Synthesis of (+)-Minfiensine -- 7.2.3 Concise Synthesis of (−)-Nakadomarin A -- 7.2.4 Collective Total Synthesis of Strychnine, Akuammicine, Aspidospermidine, Vincadifformine, Kopsinine, and Kopsanone.

7.2.5 Asymmetric Synthesis of (−)-Lycoramine, (−)-Galanthamine, and (+)-Lunarine.

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