Strategies and Tactics in Organic Synthesis

Strategies and Tactics in Organic Synthesis

1st Edition - July 29, 2013

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  • Editor: M. Harmata
  • eBook ISBN: 9780124058552
  • Hardcover ISBN: 9780080993621

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Description

A classic in the area of organic synthesis, 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, we are given 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, and we are educated, challenged and inspired by these accounts, which portray the idea that triumphs do not come without challenges. We also learn that we can meet challenges to further advance the science and art of organic synthesis, driving it forward to meet the demands of society, in discovering new reactions, creating new designs and building molecules with atom and step economies that provide solutions through function 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

Readership

Organic chemists; academic libraries, chemical and pharmaceutical companies

Table of Contents

  • Dedication

    Contributors

    Foreword

    Preface

    Chapter 1. Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines A and B

    1 Introduction and Overview

    2 Background on the Synthesis of Strychnine and Our Retrosynthesis

    3 Selected Strategies for Preparing the ABCE Tetracyclic Framework of Strychnos and Aspidosperma Alkaloids

    4 Selected Bis-Cyclization Approaches

    5 Our Approach to the ABCE Tetracycle

    6 Racemic Syntheses of Akuammicine and Strychnine

    7 Asymmetric Preparation of the ABCE Tetracycle

    8 Asymmetric Syntheses of Leuconicines A and B

    Acknowledgments

    References

    Chapter 2. Total Synthesis of the Unusual Peptide Celogentin C

    1 Introduction

    2 First Synthetic Plan and Initial Studies

    3 Synthesis of the Right-Hand Ring via Oxidative Coupling

    4 Early Attempts to Form the Left-Hand Ring

    5 Construction of the Left-Hand Ring

    6 Oxidative Coupling is Enabled by an Unexpected Additive

    7 Right-Hand Macrolactamization and One Final Surprise

    8 Anticancer Screening

    9 Conclusion

    Acknowledgments

    References

    Chapter 3. The Upside of Panic: Developing a Synthesis of Englerin A

    1 Introduction: Carbonyls and Target Selection

    2 Putting the Pieces Together: Developing a Carbonyl-Based Synthesis of Englerin A

    3 Completing Englerin A

    4 Conclusions, Thoughts, and Future Directions

    Acknowledgments

    References

    Chapter 4. Total Synthesis of (±)-Anislactone A and (±)-Merrilactone A

    1 Introduction

    2 First-Generation Synthesis of (±)-Merrilactone A and (±)-Anislactone A

    3 Conclusions

    4 Merrilactone A: Second-Generation Synthesis

    5 Conclusions

    Acknowledgments

    References

    Chapter 5. Symmetry-Driven Total Synthesis of Merrilactone A and Resolvin E2

    1 Introduction

    2 Total Synthesis of Merrilactone A

    3 Total Synthesis of Resolvin E2

    4 Conclusion

    Acknowledgments

    References

    Chapter 6. The Circuitous Journey from Malonamides to BTPhens: Ligands for Separating Actinides from Lanthanides

    1 Introduction: Partitioning of Minor Actinides and Some Fission Products Within the Nuclear Fuel Cycle

    2 Some Fundamental Aspects of the Chemistry of Minor Actinides

    3 The Required Properties of the Solvent Extraction Reagents

    4 Coextraction of Americium(III) and Europium(III): The “Easy Bit”

    5 Selective Separation of Americium(III) from Europium(III) at High Acidity: The “Hard Bit”

    6 The Future Prospects

    Acknowledgments

    References

    Chapter 7. Total Syntheses of Hamigeran B

    1 Introduction

    2 Nicolaou’s Synthesis

    3 Clive and Wang’s Syntheses

    4 Trost’s Synthesis

    5 Taber’s Synthesis

    6 Our Approaches

    7 Stoltz’s Synthesis

    8 Lau’s Synthesis

    9 Conclusion

    Acknowledgments

    References

    Chapter 8. Exploring Prins Strategies for the Synthesis of Okilactomycin

    1 Introduction

    2 Our Synthetic Approach

    3 Conclusions

    Acknowledgments

    References

    Chapter 9. Taking Risks in Complex Synthesis Design

    1 Introduction

    2 Some Examples of Architectural Self-constructions and the Power of Proximity in Complex Synthesis Design

    3 Targeting the Truly Fragile: Danishefsky’s Synthesis of Disodium Prephenate

    4 A Lesson on How to Produce a “Bent Benzene”: Baran’s Synthesis of Haouamine

    5 The Allylic Diazene Rearrangement in a Sophisticated Molecular Context: Schreiber’s Synthesis of Dynemicin A-Like Compounds

    6 Harnessing the Reactivity of Peroxyl Radicals: Corey’s Remarkable Synthesis of Prostaglandin Endoperoxide PGG2 Methyl Ester

    7 Concluding Remarks

    Acknowledgments

    References

    Chapter 10. Stereoselective Addition of Halogen to Conjugated Enynes and Its Application in the Total Synthesis of (−)-Kumausallene

    1 Introduction

    2 Halogen-Promoted 1,4-Addition to 1,3-Enynes

    3 Retrosynthetic Analysis of (−)-Kumausallene

    4 Stereoselective Synthesis of (−)-Kumausallene

    5 Conclusion

    References

    Chapter 11. Total Synthesis of Aspergillide C

    1 Introduction: Identification of the Aspergillides as Synthetic Targets

    2 Synthetic Studies on Aspergillide C

    3 Waters’ Synthesis of (+)-Aspergillide C

    4 Conclusions and Future Directions

    Acknowledgments

    References

    Index

Product details

  • No. of pages: 344
  • Language: English
  • Copyright: © Academic Press 2013
  • Published: July 29, 2013
  • Imprint: Academic Press
  • eBook ISBN: 9780124058552
  • Hardcover ISBN: 9780080993621

About the Editor

M. Harmata

M. Harmata
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

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