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.

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

?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)