Strategies and Tactics in Organic Synthesis

 
 
Academic Press
  • 1. Auflage
  • |
  • erschienen am 4. Oktober 2016
  • |
  • 294 Seiten
 
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978-0-08-100762-4 (ISBN)
 

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, 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. This book series shows how synthesis is really done.

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.

  • 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
  • Uses firsthand narrative accounts to vividly illustrate the challenges and joys involved in advancing the science of organic synthesis
1874-6004
  • Englisch
  • London
Elsevier Science
  • 10,30 MB
978-0-08-100762-4 (9780081007624)
0081007620 (0081007620)
weitere Ausgaben werden ermittelt
  • Front Cover
  • Strategies and Tactics in Organic Synthesis
  • Copyright
  • Dedication
  • Contents
  • Contributors
  • Preface
  • Chapter 1: The Long and Winding Road of the Vinigrol Synthesis: A Learning Journey
  • 1. Introduction
  • 2. Construction of the Tricyclic Framework
  • 2.1. First Approach via Domino Pericyclic Reactions11
  • 2.2. Second Approach via Hydroxy-Directed Diels-Alder Reaction11
  • 2.3. Third Approach via Diels-Alder/Claisen Reaction11
  • 2.4. Fourth Approach via Intramolecular Diels-Alder Reaction11
  • 3. Tricyclic Ring Functionalization and Unexpected Transformations
  • 4. Final Assault and Completion12
  • 5. Conclusion
  • Acknowledgments
  • References
  • Chapter 2: The Tetramic Acid Antibiotics a- and ß-Lipomycin: Total Synthesis and Assignment of the Absolute Configuration ...
  • 1. Introduction
  • 2. Hexatriene-1,6-Distannanes as Molecular Linchpins in Sequential Cross-Coupling Approaches to Polyunsaturated Natural P ...
  • 2.1. Previous Applications of Hexatriene-1,6-Distannanes as Molecular Linchpins in Natural Product Synthesis
  • 2.2. Our ``Never-Change-a-Winning-Team´´-Type Retrosynthetic Analysis of a- and ß-Lipomycin
  • 2.3. Would Our Approach to the Lipomycins Be Innovative? Yes! And Versatile? Hopefully!
  • 3. Elucidating the (Stereo)Structure of Naturally Occurring Tetramic Acids
  • 3.1. Structure Analysis of a- and ß-Lipomycin by the Discoverers
  • 3.2. (Stereo)Structural Implications of Analyzing the Genes Encoding the Biosynthesis of the Polyketide Backbone of the L ...
  • 3.3. (How) Does Synthetic Work Contribute to Tetramic Acid Natural Product Structure Elucidation?
  • 4. Synthesis of the Western Building Block or Precursor of the (Poly)Enoyltetramic Acid Motif
  • 5. Synthesis of the Eastern Building Blocks: A Library of Stereochemically Varied Iodoalkenes
  • 6. Synthesis of the Glycosyl Donor and the Glycosylated Eastern Building Block
  • 7. The Final Steps of Our Syntheses
  • 8. Without a Shadow of a Doubt? Making Doubly Sure!
  • 8.1. Regarding the Identity vs Distinctness of Our Synthetic Specimens and the Published Lipomycins
  • 8.2. Outside the Confinements of a Synthetic Laboratory: Isolating a- and ß-Lipomycin from S. aureofaciens
  • 8.3. How to Excise a Stereocenter-Containing Fragment from Natural ß-Lipomycin?
  • 8.4. Dodging a PhD Advisor's Suggestions Cannot Be Recommended-Unless the Student Transforms It to Something Superior: Tr ...
  • 8.5. Killing Two Birds with One Stone: Max Hofferberth's Synthesis of Two Full Sets of Stereoisomeric Reference Compounds
  • 8.6. The Final GLC Analyses: Nailing Down the Stereostructure of the Lipomycins for Good
  • 9. Conclusion and Outlook
  • Acknowledgments
  • References
  • Chapter 3: Step-Economical Synthesis of Clinprost and Analogs Utilizing a Novel Decarboxylation Reaction
  • 1. Introduction and Background
  • 1.1. Step Economy in Organic Synthesis
  • 1.2. Prostacyclin and Its Activity
  • 2. Retrosynthetic Analysis
  • 3. Synthesis of the Bis-Diene Building Block
  • 3.1. Orthoester Approaches
  • 3.2. Decarboxylation Approach
  • 4. Synthesis of Clinprost and Analogs
  • 4.1. Synthesis of the Bicyclic Core
  • 4.2. Synthesis of Clinprost and Analogs from the Bicyclic Core
  • 4.3. Efforts for the Synthesis of Saturated Bicyclic Analogs
  • 5. Exploration into the Novel Decarboxylation Reaction
  • 6. Conclusion
  • Acknowledgments
  • References
  • Chapter 4: Total Synthesis of Aureothin
  • 1. Introduction
  • 2. Proof of Concept
  • 2.1. State of the Art
  • 2.2. The Concept
  • 2.3. Implementing the Concept
  • 3. Assemblage of the Carbon Backbone of Aureothin
  • 3.1. First Route
  • 3.2. Second Route
  • 4. Construction of the Tetrahydrofuran Ring
  • 4.1. 1,3-Dithiane Hydrolysis
  • 4.2. Asymmetric Approach
  • 4.3. Cycloetherification
  • 4.4. Enzymatic Approach
  • 5. An Unexpected Challenge
  • 6. Conclusion
  • Acknowledgments
  • References
  • Chapter 5: (-)-Lyngbyaloside B, a Marine Macrolide Glycoside: Total Synthesis and Stereochemical Revision
  • 1. Introduction
  • 2. Total Synthesis of (-)-13-Demethyllyngbyaloside B
  • 2.1. Synthesis Plan
  • 2.2. Synthesis of Fragments
  • 2.3. Construction of Macrocycle via Esterification/RCM Strategy
  • 2.4. Completion of Total Synthesis
  • 3. Total Synthesis of the Proposed Structure of (-)-Lyngbyaloside B
  • 3.1. Initial Synthesis Plan
  • 3.2. Esterification/RCM Strategy
  • 3.3. Julia-Kocienski Olefination/Macrolactonization Strategy
  • 3.4. Acyl Ketene Macrocyclization Strategy
  • 3.5. Revised Synthesis Plan
  • 3.6. Completion of Total Synthesis
  • 4. Total Synthesis of the Correct Structure of (-)-Lyngbyaloside B
  • 4.1. Deducing the Correct Structure: NMR Analyses and Molecular Modeling
  • 4.2. Total Synthesis and Complete Stereostructure of (-)-Lyngbyaloside B
  • 5. Conclusions
  • Acknowledgments
  • References
  • Chapter 6: Total Synthesis of Ustiloxin D
  • 1. Introduction
  • 2. First Synthetic Plan and Initial Studies
  • 2.1. Early Routes to the Functionalized Isoleucine Component
  • 2.2. A Petasis Approach to the Isoleucine Allylic Donor
  • 2.3. The Joullié and Wandless Syntheses of Ustiloxin D
  • 2.4. Back to a Chiral Pool Approach to the Functionalized Isoleucine Component
  • 3. A Revised Route: AAA-Ugi Approach
  • 3.1. Establishing the Key AAA-Ugi Sequence
  • 3.2. Avoiding a Stubborn Protecting Group: The Ammonia-Ugi Approach
  • 4. Early Attempts Toward Ustiloxin A
  • 4.1. The Sulfinylnorvaline Component
  • 4.2. Dopa-Sulfinylnorvaline Adduct
  • 4.3. Forays into Early vs Late Incorporation of the Sulfinylnorvaline Moiety
  • 5. Conclusion
  • Acknowledgments
  • References
  • Chapter 7: Stereoselective Synthesis of Isochromanones with and Without Activated Spin Intermediates: Total Synthesis of ...
  • 1. Introduction
  • 2. Isochromanone Synthesis
  • 2.1. General Strategies
  • 2.2. Strategies Based on Asymmetric Ortho-Lithiations
  • 2.2.1. General Strengths and Challenges
  • 2.2.2. Asymmetric Crotylation of Axially Chiral Amides
  • 2.2.3. Synthesis of the Authentic Fragment by an Efficient Amide Cleavage
  • 2.3. Syntheses Involving Spin Intermediates
  • 2.3.1. Synthesis of Aza-Analogs via Radical Intermediates
  • 2.3.2. A Light-Triggered Iodolactonization
  • 3. Total Synthesis of Ajudazol B
  • 3.1. Retrosynthetic Analysis
  • 3.2. Fragment Syntheses
  • 3.3. Completion of the Total Synthesis
  • 4. Conclusion
  • Acknowledgments
  • References
  • Chapter 8: The Total Synthesis of WU-07047: A Selective Inhibitor of Gaq
  • 1. Introduction and Background
  • 2. A simplified lead compound for inhibiting Gq
  • 3. Synthetic approach to a simplified YM-analog
  • 4. A simplified YM-analog: the right-hand binding region
  • 5. A simplified YM-analog: the left-hand binding region
  • 6. A simplified YM-analog: putting it all together
  • Acknowledgments
  • References
  • Chapter 9: New Strategy Based on Sequential Michael/Aldol Reactions for the Asymmetric Synthesis of Cardenolides
  • 1. Introduction
  • 1.1. Introduction to Steroid Chemistry
  • 1.2. Cardiotonic Steroids
  • 1.3. Brief Overview of Synthetic Approaches to Cardenolides
  • 1.4. Overview of Michael/Aldol Cascade Strategy for the Synthesis of Cardenolides
  • 2. Development of Cu(II)-Catalyzed Asymmetric Michael Reaction
  • 2.1. Michael Reaction: The Scope of Acceptors and Donors
  • 2.2. Early Attempts to Develop Catalytic Asymmetric Michael Reaction
  • 2.3. Discovery of Cu(II)-Catalyzed Racemic Variant
  • 2.4. The Development of Bis(Oxazoline)Copper(II)-Catalyzed Asymmetric Michael Reaction
  • 2.5. Proposed Reaction Mechanism
  • 2.6. Self-Disproportionation of Enantiomers During the Purification by Achiral-Phase HPLC
  • 3. Development of Tandem Aldol Cyclization for the Formation of Cardenolides
  • 3.1. Mechanistic Consideration and Optimization Studies
  • 3.2. Computational Studies and Discussion of the Mechanism
  • 3.3. Application to the Synthesis of Cardenolides with Natural and Unnatural Configuration
  • 4. Conclusion and Outlook
  • Acknowledgments
  • References
  • Index
  • Back Cover

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