Strategies and Tactics in Organic Synthesis, Volume 8

1st Edition

Editors: Michael Harmata
Hardcover ISBN: 9780123865403
eBook ISBN: 9780123865397
Imprint: Academic Press
Published Date: 3rd August 2012
Page Count: 460
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Table of Contents





Chapter 1 Total Syntheses of Solandelactones E and F

1 Introductions and Background

2 Retrosynthetic Analysis

3 Synthesis of Solandelactone E

4 Synthesis of Solandelactone F

5 Conclusions

Chapter 2 The Marine Alkaloid Halichlorine

1 Introduction

2 The First Approach

3 The First Surprise

4 The Second Approach

5 Saved by Selenium

6 A Stereochemical Disaster—But a Blessing in Disguise

7 The Ring A Problem and the Development of a General Annulation Method

8 The Continuing Saga of Ring A

9 Formation of the Macrolactone

10 The Optical Purity Problem

11 Conclusion

Chapter 3 An Adventure in Synthesis Inspired by the Pseudolaric Acids

1 How this Chemist Came to Be

2 Pseudolaric Acids

3 The First Strategy

4 Development of the Copper Hydride-Induced Reductive Aldol Cyclization

5 The Second Strategy to Pseudolaric Acid A

6 Case 1: When Model Reactions Fail

7 Case 2: When Model Reactions Fail

8 Too Happy too Quickly, and the Importance of IR Spectroscopy

9 But it was not Time to Give Up

10 Other Natural Products

11 Epilogue

Chapter 4 Total Synthesis of Papulacandin D

1 Introduction and Background

2 Retrosynthetic Analysis

3 Preparation of the Spirocyclic Aryl Glycoside

4 Synthesis of Fatty Acid Side Chain 26 and Acylation

5 Studies on the Global Deprotection to Synthesize Papulacandin D

6 New Protecting Group Strategy

7 Global Deprotection

8 Conclusion

Chapter 5 Asymmetric Total Synthesis of the Antitumor Sesquiterpenoid (+)-Eremantholide A

1 Prologue (Karl J. Hale)

2 Introduction: Background and Previous Total Syntheses of (+)-Eremantholide A

3 The Hale–Li Retrosynthetic A


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 second-hand analysis, this book vividly demonstrates through first hand accounts how synthesis is really done and how by discovering new reactions, creating new designs and building molecules with atom and step economies, the advancement of the science of organic synthesis is providing 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 2012
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