Strategies and Tactics in Organic Synthesis
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Table of contents
- Dedicationv
- Contentsvii
- Contributorsxv
- Prefacexvii
- Forewordxix
- Chapter 1. Total Synthesis of RK-3971
- I. Introduction and Background1
- II. Retrosynthetic Analysis8
- III. Synthesis of RK-39710
- IV. Completion of the Synthesis28
- V. Summary30
- Acknowledgements32
- References and Footnotes32
- Chapter 2. A Formal Total Synthesis of the Marine Diterpenoid, Diisocyanoadociane35
- I. Introduction and Background35
- II. Synthesis Plan37
- III. Foundations and Proof of Concept40
- IV. Elaboration of the D-Ring44
- V. Elaboration of the B-ring and Exploration of the Michael Reaction46
- VI. Improved Synthesis of an Advanced Tetracyclic Intermediate51
- VII. Deoxygenation, Curtius Rearrangement, and Completion of the Synthesis53
- IX. Epilogue56
- Acknowledgments57
- References and Footnotes57
- Chapter 3. Total Syntheses of Zoapatanol59
- I. Introduction59
- II. Nicolaou’s Synthesis60
- III. Chen’s Synthesis64
- IV. Cookson’s Synthesis67
- V. Kocienski’s Synthesis69
- VI. Kane’s Synthesis73
- VII. Trost’s Synthesis78
- VIII. Our Approaches for the Total Synthesis of (+)-Zoapatanol83
- IX. Conclusion95
- References and Footnotes95
- Chapter 4. Synthesis of Molecular Tweezers and Clips by the use of a Molecular Lego Set and Their Su99
- I. Introduction and Background99
- II. Retrosynthetic Analysis102
- III. Preparation of the Molecular Building Blocks103
- IV. Synthesis of Molecular Tweezers and Clips107
- V. Thermodynamic Parameters of Host–Guest Complex Formation with Molecular Tweezers and Clips117
- VI. Host–Guest Structures and Dynamics123
- VII. Synthesis of Water-Soluble Molecular Tweezers and Clips138
- VIII. Binding of Biologically Interesting Substrates such as Enzyme Cofactors and Nucleosides in Aqu141
- IX. Conclusion149
- Acknowledgments150
- References and Footnotes150
- Chapter 5. Application of C-Glycosides in the Total Synthesis of (Š)-Gambierol154
- I. Introduction and Background154
- II. Preliminary Studies157
- III. Synthetic Strategies163
- IV. Total Synthesis of (Š)-Gambierol168
- V. Summary215
- Acknowledgements215
- References and Footnotes216
- Chapter 6. A Biomimetic Approach to the Rocaglamides Employing Photogeneration of Oxidopyryliums Der219
- I. Introduction and Background219
- II. Synthetic Strategies: A Biomimetic Approach via Photogeneration of Oxidopyryliums222
- III. Synthesis of (Š)-Methyl Rocaglate and Related Natural Products227
- IV. Enantioselective Synthesis of Rocaglamide Using Chiral Brønsted Acid232
- V. Summary239
- Acknowledgments239
- References and Footnotes239
- Chapter 7. Synthesis Studies of Dolabellanes and Transannular Processes Leading to Related Diterpene243
- I. Introduction and Background243
- II. Biosynthesis245
- III. Preliminary Studies248
- IV. Synthesis of a Dolastane via a Dolabellane Precursor252
- V. Fusicoccane Synthesis via a Dolabellane Progenitor: Total Synthesis of (+)-Fusicoauritone258
- VI. Summary264
- Acknowledgments265
- References and Footnotes265
- Chapter 8. Diphenyloxazinones: Versatile Templates for the Asymmetric Synthesis of α-Amino Acids, P268
- I. Introduction268
- II. Preparation of the Template270
- III. Glycine Electrophile272
- IV. Glycine Enolate280
- V. Other Manipulations304
- VI. Conditions to Remove the Chiral Auxiliary322
- VII. Conclusion324
- Acknowledgments324
- References and Footnotes324
- Chapter 9. Rhodium-Catalyzed Cycloisomerization Reactions of Allenes in Diversity Orientedsynthesis328
- I. Introduction328
- II. Design and Synthesis of the Pivotal Allenic-Amino Ester Intermediates336
- III. Allenic Alder-ene Reaction Affording Amino-Ester Tethered Cross-Conjugated Trienes342
- IV. Diversification of Cross-Conjugated Trienes via Diels–Alder Reactions: First Generation Triene346
- V. Design and Synthesis of a Second Generation Triene349
- VI. Synthesis and Stereoselective Diels–Alder Reaction of Novel Bicyclic Trienes353
- VII. Summary361
- Acknowledgments362
- References and Footnotes362
- Chapter 10. Hydrogen-Bond-Mediated Organic Synthesis in the Solid State368
- I. Introduction and Background368
- II. The Problem of Crystal Packing369
- III. Template-Controlled Solid-State Reactivity Using Resorcinol371
- IV. Target-Oriented Synthesis in the Solid State374
- V. Other Templates378
- VI. Conclusion381
- Acknowledgments381
- References and Footnotes381
- Chapter 11. Total Syntheses of Natural Products Using the Combined C–H Activation/Cope Rearrangeme383
- I. Introduction383
- II. Marine Natural Products from Pseudopterogorgia elisabethae384
- III. C–H Activation as a Strategic Reaction in Synthesis387
- IV. Total Synthesis of (+)-Erogorgiaene393
- V. Total Syntheses of (–)-Colombiasin A and (–)-Elisapterosin B394
- VI. Total Syntheses of (+)-Elisabethadione and Related Natural Products399
- VII. Summary404
- Acknowledgments404
- References and Footnotes405
- Chapter 12. The Total Synthesis of Amphibian Alkaloids Using the Intramolecular Schmidt Reaction408
- I. Introduction and Background408
- II. A Tryout: (Š)-Indolizidine 209B412
- III. Indolizidine 251F: Background and Synthetic Planning421
- IV. First Generation Work: Synthesis of the Key Enone and a Total Synthesis of Racemic Desmethyl 251430
- V. Intermezzo: A Few Words About Safely Working with Azides440
- VI. Development of a New Route to a Key Enone and the Total Synthesis of Alkaloid 251F442
- VII. Final Remarks455
- Acknowledgments456
- References and Footnotes457
- Chapter 13. Seduced by a Siren’s Call: Expanding Applications for Aromatic Compounds and the Synth460
- I. Burgeoning Interest in Aromatic Compounds460
- II. Why Choose a Particular Phenol Skeleton for Oxidation?464
- III. Developing Easy Access to Various Resorcinol Systems466
- IV. Total Synthesis of (±)-Epoxysorbicillinol471
- V. Plans for Chiral Auxiliaries Disintegrate472
- VI. Stereochemistry Describes an Unexpected Transition State473
- VII. Beating the Clock, Tuning the Reaction and Improving Yields474
- VIII. Controlling B-Dione Tautomerization and Protection476
- IX. A Lactic Acid-Derived Directing–Protecting Directing Group478
- X. New Methods for Cleavage of the Directing–Protecting Group482
- XI. The Total Synthesis of (+)-Rishirilide B483
- XII. New Horizons for This Method and Oxidative Dearomatizations484
- Acknowledgments488
- References and Footnotes488
- Index491
- Color Plate Section507
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. Rather than a simple presentation of data or a second-hand analysis, we are given stories that vividly demonstrate the power of the human endeavour known as organic synthesis and the creativity and tenacity of its practitioners. First hand accounts of each project tell of the excitement of conception, the frustration of failure and the joy experienced when either rational thought and/or good fortune give rise to successful completion of a project. In this book we learn how synthesis is really done and are educated, challenged and inspired by these stories, 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.
* 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
* 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