COVID-19 Update: We are currently shipping orders daily. However, due to transit disruptions in some geographies, deliveries may be delayed. To provide all customers with timely access to content, we are offering 50% off Science and Technology Print & eBook bundle options. Terms & conditions.
Strategies and Tactics in Organic Synthesis - 1st Edition - ISBN: 9780080993621, 9780124058552

Strategies and Tactics in Organic Synthesis, Volume 9

1st Edition

Editor: Michael Harmata
Hardcover ISBN: 9780080993621
eBook ISBN: 9780124058552
Imprint: Academic Press
Published Date: 7th August 2013
Page Count: 344
Sales tax will be calculated at check-out Price includes VAT/GST
Price includes VAT/GST

Institutional Subscription

Secure Checkout

Personal information is secured with SSL technology.

Free Shipping

Free global shipping
No minimum order.

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 Total Synthesis of Merrilactone A and Resolvin E2

1 Introduction

2 Total Synthesis of Merrilactone A

3 Total Synthesis of Resolvin E2

4 Conclusion



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



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



Chapter 8. Exploring Prins Strategies for the Synthesis of Okilactomycin

1 Introduction

2 Our Synthetic Approach

3 Conclusions



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



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


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





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


No. of pages:
© Academic Press 2013
7th August 2013
Academic Press
Hardcover ISBN:
eBook ISBN:

Ratings and Reviews

About the Editor

Michael Harmata

Michael 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