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Strategies and Tactics In Organic Synthesis
- 1st Edition - January 1, 1984
- Editor: Thomas Lindberg
- Language: English
- Paperback ISBN:9 7 8 - 0 - 1 2 - 4 3 1 4 9 1 - 7
- eBook ISBN:9 7 8 - 0 - 3 2 3 - 1 5 2 9 3 - 8
Strategies and Tactics in Organic Synthesis presents the chronological development of ideas and experimentation in organic synthesis. This book is organized into 13 chapters that… Read more
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Request a sales quoteStrategies and Tactics in Organic Synthesis presents the chronological development of ideas and experimentation in organic synthesis. This book is organized into 13 chapters that explore the synthetic pathways of various organic compounds. The first four chapters describe the variations in the synthesis of superphane, gibberellic acid, prostaglandin, and alkaloids. The following chapters cover the organic synthesis and biosynthesis of tylonolide, endiandric acids A-G, dodecahedrane, fomannosin, and illudol. A chapter focuses on the evolution of the total synthesis of jatrophone, an architecturally interesting macrocyclic diterpene extracted from Jatropha gossypiifolia. Another chapter discusses the heuristic principle for the stereorationale design of alkaloid syntheses. The remaining chapters discuss the approach to the total synthesis of steroids, streptonigrin, methynolide, and Prelog-Djerassi lactonic acid. Organic chemists, teachers, and students will find this book of great value.
Contributors
Preface
1. Theme and Variations: A Synthesis of Superphane
I. Introduction, Goals, and Synthetic Philosophy
II. Theme
III. Variations
IV. A Synthesis of Superphane
V. Further Variations
References
2. The Total Synthesis of Gibberellic Acid
I. Introduction
II. The Synthetic Challenge
III. The Synthetic Strategy
IV. Preliminary Studies: Stereocontrolled Elaboration of the A Ring
V. Model Studies: The Intramolecular Diels-Alder Strategy is Tested
VI. Model Studies: A Method for the Construction of the C and D Rings
VII. The Hydrindane Approach
VIII. The Hydronaphthalene Approach: (1) The Advance to Chandra's Dione
IX. The Hydronaphthalene Approach: (2) Operations on the C Ring
X. The Hydronaphthalene Approach: (3) The D Ring
XI. The Hydronaphthalene Approach: (4) Subjugation of the Β Ring
XII. The Hydronaphthalene Approach: (5) The Triumph of the Intramolecular Diels-Alder Strategy
XIII. The Hydronaphthalene Approach: (6) Stalemate at the A Ring
XIV. The Total Synthesis of Gibberellic Acid
References
3. A Prostaglandin Synthesis
I. Introduction
II. 7-Oxaprostaglandins
III. Prostaglandin F2α
IV. 13,14-Dehydroprostaglandins
References
4. Synthesis of Indole Alkaloids
I. Introduction
II. Early Thoughts
III. Initial Results: First Phase
IV. Flexible Strategy-Flexible Tactics: Second Phase
V. Synthesis of (±)-Aspidospermidine: Third Phase
VI. Reverse Roles: Fourth Phase
VII. Completion of the "Model Work"
VIII. New Territory
References
5. Synthesis of Tylonolide, the Aglycone of Tylosin
I. Introduction
II. General Strategy
III. Preliminary Work
IV. Synthesis
V. Concluding Remarks
References
6. Pericyclic Reactions in Organic Synthesis and Biosynthesis: Synthetic Adventures with Endiandric Acids A-G
I. Introduction: The Appealing Endiandric Acid Cascade
II. Retrosynthetic Analyis of Endiandric Acids A-G
III. Synthesis of the Key Bicyclic Intermediate
IV. Functionalization of the Bicyclic Intermediate: Synthesis of Endiandric Acids D, E, F, and G
V. The Intramolecular Diels-Alder Reactions: Synthesis of Endiandric Acids A, B, and C
VI. Conclusions
References
7. Plato's Solid in a Retort: the Dodecahedrane Story
I. Introduction
II. The Decision against Convergency and Building of the Cornerstone
III. A Retrosynthetic Glimpse and Symmetry Considerations
IV. Arrival at the "Closed" and "Open" Dilactones
V. Chemical Reactivity of the "Open" Dilactone
VI. Functionalization Reactions of the "Closed" Dilactone
VII. (C2)-Dioxa-C20-Octaquinane, a Heterocyclic Trisecododecahedrane
VIII. The Pilot Photochemical Experiment
IX. Trisecododecahedranes via Dichloro Diester Reduction
X. The Monoseco Level of Elaboration
XI. Installation of the Final Bond: Formation of 1,16-Dimethyldodecahedrane
XII. Further Developments
XIII. Controlled Monosubstitution and Isolation of an Isododecahedrane
XIV. Bypassing the Unwanted Reaction Pathway
XV. (CH)20: The Parent Dodecahedrane
References
8. The Synthesis of Fomannosin and Illudol
I. Introduction
II. The Target
III. The Ketene Cycloaddition Approach to Fomannosin
IV. Synthesis of Illudol and Fomannosin from a Common Intermediate
V. Summary
References
9. Evolution of a Synthetic Strategy: Total Synthesis of Jatrophone
I. Introduction
II. General Background
III. A Strategy for the Total Synthesis of Jatrophone
IV. Synthesis of Simple 3(2H)-Furanones: The First Major Spin-Off of the Jatrophone Program
V. A Successful Conclusion to Phase I: Synthesis of 3(2H)-Furanone 21
VI. Synthesis of α-Hydroxymethylcyclopentenone: An Initial Solution
VII. An Alternate Approach to α-Hydroxymethylcyclopentenone: Development of a Versatile Latent α-Ketovinyl Anion Equivalent
VIII. Synthesis of the Pentenomycins, Their Epimers, and Dehydropentenomycin: A Major Diversion
IX. Return to the Jatrophone Problem: A Successful Failure
X. Development of An Alternative 3(2H)-Furanone Protocol: A New 1,3-Diketone Synthesis
XL Exploitation of the Improved 3(2H)-Furanone Protocol
XII. Macrocyclization: A Difficult Step
XIII. Completion of Phase II: Synthesis of Normethyljatrophone
XIV. Phase III: The Stereochemical Problem
XV. Total Synthesis of Jatrophone and Its Epimer: The Final Goal
XVI. Further Diversions during the Jatrophone Synthetic Program
XVII. Reactions of Simple 3(2H)-Furanones and Furadienones with Propanethiol
XVIII. Jatrophone Analogs: cis- and trans-Normethyljatropholactones
XIX. Isolation of Three New Jatrophone Derivatives
XX. Interplay of Structure and Conformation of the Jatrophone Nucleus vis-a-vis Antitumor Activity
References
10. On the Stereochemistry of Nucleophilic Additions to Tetrahydropyridinium Salts: A Powerful Heuristic Principle for the Stereorationale Design of Alkaloid Syntheses
Text
References
11. A Nonbiomimetic Approach to the Total Synthesis of Steroids: the Transition Metalcatalyzed Cyclization of Alkenes and Alkynes
I. Introduction
II. Model Studies in Cobalt-Mediated Alkyne Cyclizations
III. Cobalt-Mediated [2 + 2 + 2]Cycloadditions en Route to Annulated Cyclohexadienes
References
12. Evolution of a Strategy for Total Synthesis of Streptonigrin
I. Introduction
II. Synthetic Strategy
III. Preliminary AB-Ring Studies
IV. Preliminary CD-Ring Studies
V. Synthesis of Streptonigrin
References
13. Methynolide and the Prelog-Djerassi Lactonic Acid: an Exercise in Stereocontrolled Synthesis
I. Introduction
II. Excursions from 2,4-Dimethylfuran
III. Further Expeditions from 8-Oxabicyclo[3.2.1]octanes
IV. The Prelog-Djerassi Lactonic Acid (4)
V. A Cycloheptanoid Route to Methynolide
References
Index
- No. of pages: 384
- Language: English
- Edition: 1
- Published: January 1, 1984
- Imprint: Academic Press
- Paperback ISBN: 9780124314917
- eBook ISBN: 9780323152938
TL
Thomas Lindberg
Affiliations and expertise
G. D. Searle Research and Development