Description
Book SynopsisOne 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.
Trade Review?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)
Table of ContentsPreface 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
