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Organic Synthesis: The Disconnection Approach, 2nd Edition

ISBN: 978-0-470-71237-5
342 pages
December 2008
Organic Synthesis: The Disconnection Approach, 2nd Edition (0470712376) cover image
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.

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1. Introduction: Planning Organic Syntheses..

2. Synthons and Reagents: Aromatic Compounds.

3. Strategy I: The Order of Events.

4. One-Group C-X Disconnections.

5. Chemoselectivity.

6. Two-Group C-X Disconnections.

7. Strategy III.

8. Amine Synthesis.

9. Protecting Groups.

10. One Group C-C Disconnections I: Alcohols.

11. General Strategy A: Choosing Disconnections.

12. Stereoselectivity A.

13. One Group C-C Disconnections II: Carbonyl Compounds.

14. Regioselectivity.

15. Alkene Synthesis.

16. Strategy VII: Use of Acetylenes.

17. Diels-Alder.

18. Strategy VIII: Carbonyl Condensations.

19. 1,3-diCO Compounds.

20. Control in C=O Condensations.

21. 1,5-diCO Compounds.

22. Nitro Groups.

23. 1,2-diCO Compounds.

24. Radicals.

25. 1,4-diCO Compounds.

26. Reconnection.

27. 1,6-diCO Compounds.

28. Strategy of C=O Disconnections.

29. Saturated Heterocycles.

30. Cyclopropanes.

31. Rearrangements.

32. Four-Membered Rings.

33. Ketenes.

34. Five-Membered Rings.

35. Pericyclic Reactions.

36. Six-Membered Rings.

37. Strategy of Ring Synthesis.

38. Stereoselectivity B.

39. Aromatic Heterocycles.

40: Advanced Strategy.

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  • Fully revised and updated to reflect 25 years of advances in organic synthesis: new examples and synthetic pathways have been added
  • Adopts a modern look, with a larger format, and schemes and structures now drawn in ChemDraw format
  • Additional material has been added to take the student to the level required by the sequel, “Organic Synthesis: Strategy and Control”
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  • A complete course in retrosynthetic analysis for advanced organic students – describes and illustrates the key concepts involved in how to use retrosynthetic analysis to design synthetic routes
  • By working through this book students will develop their skills in analyzing synthetic challenges, and build a toolkit of strategies for planning new syntheses
  • Revised and updated to reflect 25 years of advances in organic synthesis: new examples and synthetic pathways have been added
  • The later chapters on more advanced techniques have extensive new material based on courses that the authors give in the pharmaceutical industry
  • Includes many examples drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavoring compounds, dyestuffs, and other intermediates used in more advanced synthetic work.

  • Provides reasons for wishing to synthesize each compound 

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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)

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