Strategies and Tactics in Organic Synthesis, Volume 9

1st Edition

Editors: Michael Harmata
Hardcover ISBN: 9780080993621
eBook ISBN: 9780124058552
Imprint: Academic Press
Published Date: 7th August 2013
Page Count: 344
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Table of Contents





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



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



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



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



Chapter 5. Symmetry-Driven T


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


Organic chemists; academic libraries, chemical and pharmaceutical companies


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Academic Press
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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