Strategies and Tactics in Organic Synthesis, Volume 11

• Dedication
• Preface
• Chapter 1: Acortatarin A: Spiroketalization Methods and Synthesis
  • Abstract
  • 1 Introduction
  • 2 Evolution of Au- and Pd-Catalyzed Spiroketalization Methods
  • 3 Acortatarin A and Related Natural Products
  • 4 Synthetic Efforts via Pd-Catalyzed Spiroketalization
  • 5 Conclusion
  • Acknowledgments
• Chapter 2: Devising New Syntheses of the Alkaloid Galanthamine, a Potent and Clinically Deployed Inhibitor of Acetylcholine Esterase
  • Abstract
  • 1 Introduction
  • 2 Studies on the Synthesis of Galanthamine—A Potted History
  • 3 A First-Generation Chemoenzymatic Synthesis of (+)-Galanthamine
  • 4 Total Syntheses of Members of the Ribisin Class of Neurologically Active Natural Product Inspire a Second-Generation Chemoenzymatic Approach to (+)-Galanthamine
  • 5 An Abortive, Radical-Based Approach to (±)-Galanthamine
  • 6 Doing Things the Hard Way—De Novo Construction of the Aromatic C-Ring as a Focal Point
  • 7 Conclusions
  • Acknowledgments
• Chapter 3: Discodermolide: Total Synthesis of Natural Product and Analogues
  • Abstract
  • 1 Introduction
  • 2 Synthetic Approach and Synthetic Methods Development
  • 3 Total Synthesis of (+)-DDM
  • 4 Conception, Synthesis, and Biological Evaluation of DDM Analogues
  • 5 Conclusion
  • Acknowledgments
• Chapter 4: A Walk Across Africa with Captain Grant: Exploring Mycobacterium ulcerans Infection with Mycolactone Analogs
  • Abstract
  • 1 Introduction
  • 2 Synthetic Strategy of the Mycolactone A/B Analogs
  • 3 Exploration of the Biology Induced by Mycolactone A/B Analogs
  • 4 Conclusions and Future Prospects
  • Acknowledgments
• Chapter 5: Total Synthesis of the Fungal Metabolite Virgatolide B
  • Abstract
  • 1 Introduction
  • 2 First Synthetic Strategy
  • 3 Second Synthetic Strategy
  • 4 Total Synthesis of Virgatolide B
  • 5 Conclusion
  • Acknowledgments
• Chapter 6: The Role of Design, Serendipity, and Scientific Competition in the Development of Oxidative Coupling Reactions
  • Abstract
  • 1 Introduction
  • 2 Synthesis of Biaryls via Oxidative Cross-Coupling
  • 3 Controlling Regioselectivity for Indole Substrates
  • 4 Mechanism of C–H Palladation in Oxidative Coupling Reactions
  • 5 Returning to Oxidative Amination
  • 6 Conclusion
  • Acknowledgements
• Chapter 7: Overcoming Electronics with Strategy: Development of an Efficient Synthesis of the HIV Attachment Inhibitor Prodrug, BMS-663068
  • Abstract
  • 1 Introduction
  • 2 Route Selection
  • 3 Lessons Discovered During Process Development
  • 4 Conclusion
  • Acknowledgments
• Chapter 8: Synthesis of Alkaloids Containing a Quinolizidine Core by Means of Strategies Based on a Hydroformylation Reaction
  • Abstract
  • 1 Introduction
  • 2 Aza-Sakurai–Hosomi Reaction Associated with Hydroformylation
  • 3 Hydroformylation Reaction as Trigger of Domino Reaction
  • 4 Hydroformylation of Bis-Homoallylazides
  • 5 Conclusion
  • Acknowledgments
• Chapter 9: Total Synthesis of Sorbicillactone A: An Inspiration for Methodology and Catalyst Development
  • Abstract
  • 1 Introduction
  • 2 Background
  • 3 Model Studies
  • 4 Synthesis of Sorbicillactone A and 9-epi-Sorbicillactone A
  • 5 Conclusion
  • Acknowledgements
• Chapter 10: Total Synthesis of (−)-7-Deoxyloganin Exploiting N-Heterocyclic Carbene Catalysis with α,β-Unsaturated Enol Esters
  • Abstract
  • 1 Background
  • 2 Iridoid Glycoside Natural Products
  • 3 Total Synthesis of (−)-7-Deoxyloganin
  • 4 An Improved Strategy
  • 5 Conclusions
• Chapter 11: The Realization of an Oxidative Dearomatization–Intramolecular Diels–Alder Route to Vinigrol
  • Abstract
  • 1 Introduction
  • 2 Wessely Oxidation Studies
  • 3 Adler–Becker Oxidation Attempts
  • 4 Pyrogallol Dearomatizations (Part 1)
  • 5 Pyrogallol Dearomatizations (Part 2)
  • 6 Pyrogallol Dearomatizations (Part 3)
  • 7 Pyrogallol Dearomatizations (Part 4)
  • 8 Fragmentations
  • 9 Installing the C-14 Isopropyl and C-4 Hydroxyl Groups
  • 10 Endgame—Deprotection of a New Protecting Group
  • 11 Conclusion
  • Acknowledgments
• Chapter 12: Total Synthesis of Communesin F and Perophoramidine
  • Abstract
  • 1 Introduction
  • 2 Early Methodology Studies for the Construction of the Common Pentacyclic Framework of Communesins and Perophoramidine via CRI Reaction
  • 3 Total Synthesis of (±)-Communesin F
  • 4 Asymmetric Total Synthesis of (+)-Perophoramidine
  • 5 Conclusions
  • Acknowledgments
• Index

Strategies and Tactics in Organic Synthesis provides a forum for investigators to discuss their approach to the science and art of organic synthesis. Rather than a simple presentation of data or a secondhand analysis, this classic provides stories that vividly demonstrate the power of the human endeavor known as organic synthesis and the creativity and tenacity of its practitioners.

Firsthand accounts of each project tell of the excitement of conception, the frustration of failure, and the joy experienced when either rational thought or good fortune gives rise to the successful completion of a project. This book series shows how synthesis is really done. Readers will be educated, challenged, and inspired by these accounts, which portray the idea that triumphs do not come without challenges.

This innovative approach also helps illustrate how challenges to further advance the science and art of organic synthesis can be overcome, driving the field forward to meet the demands of society by discovering new reactions, creating new designs, and building molecules with atom and step economies that provide functional solutions to create a better world.

• Presents state-of-the-art developments in organic synthesis
• Provides insight and offers new perspective to problem-solving
• Written by leading experts in the field
• Uses firsthand narrative accounts to illustrate vividly the challenges and joys involved in advancing the science of organic synthesis

Organic chemists; academic libraries; chemical and pharmaceutical companies