Strategies and Tactics in Organic Synthesis

Strategies and Tactics in Organic Synthesis

1st Edition - November 11, 2021

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  • Editor: Michael Harmata
  • Paperback ISBN: 9780128222126
  • eBook ISBN: 9780128217573

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Strategies and Tactics in Organic Synthesis, Volume 15, 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 present 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. 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

  • Provides insight and offers new perspective to problem-solving
  • Presents state-of-the-art developments in organic synthesis
  • Written by leading experts in the field
  • Uses firsthand narrative accounts to vividly illustrate the challenges and joys involved in advancing the science of organic synthesis


Organic chemists specializing in organic synthesis working in academia, government laboratories, and industry. Analytical Chemists, Biochemists, Pharmaceutical Scientists and Chemical Engineers

Table of Contents

  • Cover image
  • Editorial Board
  • Title page
  • Table of Contents
  • Copyright
  • Dedication
  • Contributors
  • Preface
  • Chapter 1. Amaryllidaceae isocarbostyril alkaloids
  • 1. Introduction
  • 2. Synthetic strategy
  • 3. Pancratistatins
  • 4. Narciclasine and lycoricidine
  • 5. Conclusion
  • Chapter 2. Enzymatic dihydroxylation of aromatic compounds: Nature's unique reaction and its impact on the synthesis of natural products
  • 1. Introduction
  • 2. History and biochemistry
  • 3. Emergence in enantioselective synthesis
  • 4. Natural products and related derivatives attained from cis-dihydrodiols
  • 5. Epilogue
  • 6. Notes
  • 7. Note added in proof
  • Chapter 3. Intermolecular oxidopyrylium [5+2] cycloaddition chemistry and its application toward the synthesis and study of highly oxygenated troponoids
  • 1. Introduction
  • 2. History of oxidopyrylium [5+2] cycloaddition approach to troponoid synthesis
  • 3. Intermolecular 3-hydroxy-4-pyrone-based oxidopyrylium [5+2] cycloaddition
  • 4. Application of oxidopyrylium cycloadducts in the synthesis and study of troponoids
  • 5. Conclusion
  • Chapter 4. Aryne-mediated construction of fluorene skeletons and its applications to total synthesis of selaginpulvilins
  • 1. Introduction
  • 2. Selaginpulvilins and related natural products
  • 3. Review of synthetic strategies toward selaginpulvilins
  • 4. Hexadehydro Diels–Alder reaction
  • 5. Total synthesis of selaginpulvilin C and D
  • 6. Conclusion
  • Chapter 5. Cycloisomerizations across three states: the total synthesis of gelsenicine
  • 1. Introduction
  • 2. Cycloisomerization and the Schisandra natural products
  • 3. Enantiospecific cycloisomerization of ethereal enynes
  • 4. Gelsemium alkaloid synthesis
  • 5. Conclusion
  • Chapter 6. Tetrapetalones ruminations, trials and tribulations
  • 1. Ruminations
  • 2. First impressions
  • 3. Recollections of tetramic and tetronic acids past
  • 4. Porco's [4+3] proposition
  • 5. Nails on hand
  • 6. Second swing for the fence
  • 7. A scrubbed launch
  • 8. Sarpong's reckoning
  • 9. A failure to divinylate
  • 10. Revenge of the interconverting dienes
  • 11. A new hope
  • 12. Return to nitroaromatics
  • 13. A robust strategy
  • 14. Seven carbons for brother Tom
  • 15. The quaternary conundrum
  • 16. Applying vinyl siding
  • 17. Five-membered death punch
  • 18. A friend in need
  • 19. Frontier's aglycone
  • 20. Desperate measures
  • 21. Wood’s synthesis
  • 22. Life of Bai
  • Chapter 7. The synthesis of herqulines B and C
  • 1. The herquline alkaloids
  • 2. Tang's biosynthesis of the herqulines
  • 3. Reported attempts toward the herqulines
  • 4. Inspiration from Hutton's synthesis of mycocyclosin
  • 5. Development of a scalable macrocyclization for mycocyclosin analogue synthesis
  • 6. Early Birch reduction investigations on mycocyclosin core
  • 7. A revised retrosynthetic analysis of the herqulines
  • 8. An oxidative dearomatization/reduction approach for herquline synthesis
  • 9. Installation of the final cyclohexenone ring
  • 10. Completion of herqulines B and C
  • 11. Wood and Baran's total synthesis of herqulines B and C
  • 12. Conclusion
  • Chapter 8. First total synthesis of the dimeric naphthoquinonopyrano-γ-lactone natural product (−)-crisamicin A. How procrastination may be of help in binaphthyl synthesis
  • 1. Naphthoquinonopyrano-γ-lactone natural products
  • 2. The naphthoquinonopyrano-γ-lactone natural product crisamicin A
  • 3. The first stereoselective total synthesis of a dimeric naphthoquinonopyrano-γ-lactone ever: (+)-γ-actinorhodin (Neumeyer and Brückner)
  • 4. Literature routes to(wards) the dimeric naphthoquinonopyrano-γ-lactone natural product (−)-crisamicin A
  • 5. A biaryl strategy for the total synthesis of (−)-crisamicin A with some promise for non-naphthoquinonopyrano-γ-lactone targets: a late-stage borylation/dimerization tandem approach to polynuclear biaryls
  • 6. Our initial retrosynthetic analysis of (−)-crisamicin A: envisaging an aryne/siloxyfuran Diels–Alder approach
  • 7. Reconsidering our synthetic strategy from scratch: hoping to be better off without a Diels–Alder reaction
  • 8. Conclusion
  • Chapter 9. Strategies and discoveries leading to the synthesis of trichoaurantianolide natural products
  • 1. Introduction
  • 2. Retrosynthetic analysis
  • 3. Preliminary investigations
  • 4. Tactics for functionalization of the bridgehead substituent
  • 5. Revisiting the original plan
  • 6. New plan and renewed opportunities
  • 7. Completion of the total synthesis
  • 8. Conclusion
  • Chapter 10. 4-exo-dig cyclocarbopalladation, discovery and application in the synthesis of complex polycyclic molecules
  • 1. Introduction
  • 2. Discovery of the 4-exo-dig cyclocarbopalladation and its application to the synthesis of strained polycyclic compounds
  • 3. The 4-exo-dig cyclocarbopalladation for the synthesis of fenestradienes and cyclooctatrienes
  • 4. The 4-exo-dig cyclocarbopalladation in the synthesis of cyclooctatetraenes
  • 5. General conclusion
  • Index

Product details

  • No. of pages: 444
  • Language: English
  • Copyright: © Elsevier 2021
  • Published: November 11, 2021
  • Imprint: Elsevier
  • Paperback ISBN: 9780128222126
  • eBook ISBN: 9780128217573

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

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