One approach to organic synthesis is retrosynthetic analysis. With this approach a chemist will start with the structure of their target molecule and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials. This “disconnection” approach to synthesis is now a fundamental part of every organic synthesis course.
Organic Synthesis: The Disconnection Approach, 2nd Edition introduces this important technique, to help students to design their own organic syntheses. There are forty chapters: those on the synthesis of given types of molecules alternate with strategy chapters in which the methods just learnt are placed in a wider context. The synthesis chapters cover many ways of making each type of molecule starting with simple aromatic and aliphatic compounds with one functional group and progressing to molecules with many functional groups. The strategy chapters cover questions of selectivity, protection, stereochemistry, and develop more advanced thinking via reagents specifically designed for difficult problems.
Examples are drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavouring compounds, dyestuffs, monomers, and intermediates used in more advanced synthetic work. Reasons for wishing to synthesise each compound are given.
This second edition has been fully revised and updated with a modern look. Recent examples and techniques are included and illustrated additional material has been added to take the student to the level required by the sequel, “Organic Synthesis: Strategy and Control”.
Several chapters contain extensive new material based on courses that the authors give to chemists in the pharmaceutical industry.
Organic Synthesis: The Disconnection Approach, 2nd edition provides a full course in retrosynthetic analysis for chemistry and biochemistry students and a refresher for organic chemists working in industry and academia.
Preface ix General References xi 1. The Disconnection Approach 1 2. Basic Principles: Synthons and Reagents Synthesis of Aromatic Compounds 7 3. Strategy I: The Order of Events 17 4. One-Group C–X Disconnections 23 5. Strategy II: Chemoselectivity 29 6. Two-Group C–X Disconnections 35 7. Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategy 45 8. Amine Synthesis 53 9. Strategy IV: Protecting Groups 61 10. One Group C–C Disconnections I: Alcohols 69 11. General Strategy A: Choosing a Disconnection 77 12. Strategy V: Stereoselectivity A 83 13. One Group C–C Disconnections II: Carbonyl Compounds 93 14. Strategy VI: Regioselectivity 101 15. Alkene Synthesis 107 16. Strategy VII: Use of Acetylenes (Alkynes) 115 17. Two-Group C–C Disconnections I: Diels-Alder Reactions 121 18. Strategy VIII: Introduction to Carbonyl Condensations 129 19. Two-Group C–C Disconnections II: 1,3-Difunctionalised Compounds 133 20. Strategy IX: Control in Carbonyl Condensations 139 21. Two-Group C–C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation 151 22. Strategy X: Aliphatic Nitro Compounds in Synthesis 161 23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds 167 24. Strategy XI: Radical Reactions in Synthesis 177 25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds 185 26. Strategy XII: Reconnection 193 27. Two-Group C–C Disconnections VI: 1,6-diCarbonyl Compounds 199 28. General Strategy B: Strategy of Carbonyl Disconnections 207 29. Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocycles 217 30. Three-Membered Rings 229 31. Strategy XIV: Rearrangements in Synthesis 237 32. Four-Membered Rings: Photochemistry in Synthesis 245 33. Strategy XV: The Use of Ketenes in Synthesis 251 34. Five-Membered Rings 255 35. Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings 261 36. Six-Membered Rings 269 37. General Strategy C: Strategy of Ring Synthesis 279 38. Strategy XVII: Stereoselectivity B 289 39. Aromatic Heterocycles 301 40. General Strategy D: Advanced Strategy 313 Index 325
Dr Stuart Warren, Department of Chemistry, University of Cambridge, UK Dr Warren is the author of the bestselling textbooks Organic Synthesis: The Disconnection Approach (Wiley), Organic Synthesis: Strategy and Control (Wiley) and Organic Chemistry (OUP). Dr Paul Wyatt, School of Chemistry, University of Bristol, UK Dr Wyatt is Director of Undergraduate Studies for the School of Chemistry at Bristol University and also Director of BRISTOL ChemLabS - a HEFCE Centre for Excellence in Teaching & Learning. He is co-author, with Warren, of Organic Synthesis: Strategy and Control.
Reviews for Organic Synthesis: The Disconnection Approach
?The authors have succeeded admirably in the updating of a classic in the pedagogy of organic chemistry.? ( Journal of Medicinal Chemistry , August 2009) ?This book is suitable for advanced undergraduate students, researchers and professional chemists. Both the writing and the diagrams are simple and clear.? ( Reviews, May 2009)
