Description
Book SynopsisOne approach to organic synthesis is retrosynthetic analysis. With this approach chemists start with the structures of their target molecules 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 book provides an excellent and pragmatic panorama of the various aspects of disconnective strategies, whilst keeping in mind the importance of protective strategies." (
Reviews, December 2010)
Table of ContentsPreface vii
General References ix
1. The Disconnection Approach 1
2. Basic Principles: Synthons and Reagents: Synthesis of Aromatic Compounds 5
3. Strategy I: The Order of Events 11
4. One-Group C–X Disconnections 15
5. Strategy II: Chemoselectivity 21
6. Two-Group C–X Disconnections 29
7. Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategy 35
8. Amine Synthesis 41
9. Strategy IV: Protecting Groups 49
10. One-Group C–C Disconnections I: Alcohols 55
11. General Strategy A: Choosing a Disconnection 61
12. Strategy V: Stereoselectivity A 67
13. One-Group C–C Disconnections II: Carbonyl Compounds 75
14. Strategy VI: Regioselectivity 81
15. Alkene Synthesis 87
16. Strategy VII: Use of Acetylenes (Alkynes) 93
17. Two-Group C–C Disconnections I: Diels-Alder Reactions 99
18. Strategy VIII: Introduction to Carbonyl Condensations 105
19. Two-Group C–C Disconnections II: 1,3-Difunctionalised Compounds 111
20. Strategy IX: Control in Carbonyl Condensations 115
21. Two-Group C–C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation 123
22. Strategy X: Aliphatic Nitro Compounds in Synthesis 129
23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds 133
24. Strategy XI: Radical Reactions in Synthesis 139
25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds 147
26. Strategy XII: Reconnection 153
27. Two-Group C–C Disconnections VI: 1,6-diCarbonyl Compounds 159
28. General Strategy B: Strategy of Carbonyl Disconnections 165
29. Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocycles 173
30. Three-Membered Rings 181
31. Strategy XIV: Rearrangements in Synthesis 189
32. Four-Membered Rings: Photochemistry in Synthesis 195
33. Strategy XV: The Use of Ketenes in Synthesis 201
34. Five-Membered Rings 207
35. Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings 213
36. Six-Membered Rings 221
37. General Strategy C: Strategy of Ring Synthesis 227
38. Strategy XVII: Stereoselectivity B 235
39. Aromatic Heterocycles 245
40. General Strategy D: Advanced Strategy 255
Index 263
