Strategies and Tactics in Organic Synthesis - 1st Edition - ISBN: 9780081000236, 9780081000465

Strategies and Tactics in Organic Synthesis, Volume 11

1st Edition

Editors: Michael Harmata
eBook ISBN: 9780081000465
Hardcover ISBN: 9780081000236
Imprint: Elsevier
Published Date: 11th August 2015
Page Count: 442
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Table of Contents

  • 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.

Key Features

  • 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


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Ratings and Reviews

About the Editors

Michael Harmata Editor

Professor Michael Harmata graduated from the University of Illinois-Chicago with honors and highest distinction in chemistry.

In 1980, he began graduate studies in chemistry at the University of Illinois-Champaign/Urbana where he was awarded a University Teaching Fellowship. He worked with Professor Scott E. Denmark on the invention of the carbanion-accelerated Claisen rearrangement. In his second year of study, he was awarded an Eastman Kodak Research Fellowship.

Upon graduation in 1985, he was awarded an NIH postdoctoral fellowship which he used to study with Professor Paul A. Wender at Stanford University, where he worked on the synthesis of the neocarzinostatin chromophore.

In 1986, Prof. Harmata began his independent career at the University of Missouri-Columbia. He became an Associate Professor in 1992 and a full professor in 1998. In 2000, he was named the Norman Rabjohn Distinguished Professor of Chemistry in recognition of his achievements in research and teaching. In 1998, he received a research fellowship from the Alexander von Humboldt Foundation and stayed for a year at the University of Göttingen where he was affiliated with the groups of Professors Reinhard Brückner and Lutz. F. Tietze. In 2000, he served as chair of the Gordon conference on Organic Reactions and Processes. In 2010, he was named the first Justus Liebig Professor of Chemistry at the Justus Liebig Üniversität in Giessen, Germany. In 2011, he was a JSPS fellow. He has been a visiting professor in Giessen and Strasbourg and has delivered over 180 invited lectures in the United States and Europe. He is a member of the American Chemical Society, Gesellschaft Deutscher Chemiker, International Society of Heterocyclic Chemistry, and the Alexander von Humboldt Association of America.

Affiliations and Expertise

University of Missouri, MO, USA