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Classics in Total Synthesis III

Classics in Total Synthesis III

K. C. Nicolaou, Jason S. Chen

ISBN: 978-3-527-32958-8

Apr 2011

770 pages

Select type: Hardcover

In Stock

$170.00

Description

K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry

Retaining his excellent, proven approach, world-famous chemist and passionate teacher K.C. Nicolaou compiles here the important strategies and tools employed to construct complex molecules. For a total of 42 syntheses of 25 challenging natural products he explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections for easier understanding, and contrasting these to other synthetic methods. Similar to its predecessors and completing the trilogy, this textbook analyzes the syntheses in a didactic manner, with several chapters including mini-reviews of key methodologies, and an emphasis on the history, mechanism, scope, and generality of the reactions. In contrast to the first two volumes, this new one features full-color frontispieces.
A wonderful tool for learning and teaching and a must-have for all current and future organic and biochemists.
Chapter 1. Introduction: The Advancing Field of Total Synthesis.

1.1   Targets.

1.2   Strategies and Methods.

1.3   Classics in Total Synthesis III.

Chapter 2. Tetrodotoxin (Y. Kishi, J. Du Bois) (1972; 2003).

2.1 Introduction.

2.2 Kishi’s Retrosynthetic Analysis and Strategy.

2.3 Kishi’s Totla Synthesis.

2.4 Du Bois’ Retrosynthetic  Anaysis and Strategy.

2.5 Du Bois’ Total Synthesis.

2.6 Conclusion.

Chapter 3. Discodermolide (Novartis: S. J. Mickel, I. Paterson, A. B. Smith, III) (2004).

3.1 Introduction.

3.2 Retrosynthetic Analysis and Strategy.

3.3 Total synthesis.

3.4 Conclusion.

Chapter 4. Azaspiracid – I (K. C. Nicolaou, D. A. Evans) (2004, 2006, 2007).

4.1 Introduction.

4.2 Nicolaou’s Retrosynthetic Analysis and Stratrgy.

4.3 Nicolaou’s Total Synthesis.

4.4 Evans’ Retrosynthetic Analysis and Strategy.

4.5 Evans’ Total Synthesis.

4.6 Conclusion.

Chapter 5. Thiostrepton (K. C. Nicolaou) (2004).

5.1 Introduction.

5.2 Retrosynthetic Analysis and Strategy.

5.3 Total Synthesis.

5.4 Conclusion.

Chapter 6. Pentacycloanammoxic Acid Methyl Ester (E. J. Corey (2004, 2006).

6.1 Introduction.

6.2 First-Generation Retrosynthetic Analysis and Strategy.

6.3 First-Generation Total Synthesis.

6.4 Second-Generation Retrosynthetic Analysis and Strategy.

6.5 Second-Generation Total Synthesis.

6.6 Conclusion.

Chapter 7. Littoralisone, Oseltamivir (Tamiflu®), and Hirsutellone B (D. W. C. MacMillan, Y. Hayashi, K. C. Nicolaou ) (2005, 2009, 2009).

7.1 Introduction.

7.2 Introduction to Littoralisone.

7.3 Total Synthesis of Littoralisone.

7.4 Introduction to Oseltamivir (Tamiflu®).

7.5 Total Synthesis of Oseltamivir (Tamiflu®).

7.6 Introduction to Hirsutellone B.

7.7 Total Synthesis of Hirsutellone B.

7.8 Conclusion.

Chapter 8. Rubicordifolin and Rubiocolin B (D. Trauner) (2005, 2008).

8.1 Introduction.

8.2 Retrosynthetic Analysis of Rubicordifolin.

8.3 Total Synthesis of Rubicordifolin.

8.4 Retrosynthetic Analysis of Rubioncolin B.

8.5 Total Synthesis of Rubioncolin B.

8.6 Conclusion.

Chapter 9. Cyanthiwigins U and F (A. J. Phillips, B. M. Stoltz) (2005, 2008).

9.1 Introduction.

9.2 Phillips’ Retrosynthesis Analysis and Strategy.

9.3 Phillips Total Synthesis.

9.4 Stoltz’ Retrosynthetic Analysis and Strategy.

9.5 Stoltz’ Total Synthesis.

9.6 Conclusion.

Chapter 10. Stephacidin B (A. G. Myers, P. S. Baran, R. M. Williams) (2005, 2005, 2007).

10.1 Introduction.

10.2 Myers’ Retrosynthetic Analysis and Strategy.

10.3 Myers’ Total Synthesis.

10.4 Baran’s Retrosynthetic Analysis and Strategy.

10.5 Baran’s Total Synthesis.

10.6 Williams’ Retrosynthetic Analysis and Strategy.

10.7 Williams’ Total Synthesis.

10.8 Conclusion.

Chapter 11. Abyssomicin C and atrop-Abyssomicin C (E. J. Sorensen, K. C. Nicolaou) (2005, 2006).

11.1 Introduction.

11.2 Sorensen’s Retrosynthetic Analysis and Strategy.

11.3 Sorensen’s Total Synthesis of Abyssomicin C.

11.4 Nicolaou’s Retrosynthetic Analysis and Strategy.

11.5 Nicolaou’s Total Synthesis of Abyssomicin C and atrop-Abyssomicin C.

11.6 Conclusion.

Chapter 12. Tetracycline (A. G. Myers). (2005, 2007).

12.1 Introduction.

12.2 Retrosynthetic Analysis and Strategy.

12.3 Total Synthesis.

12.4 Conclusion.

Chapter 13. Bisanthraquinone Natural Products (K.Nicolaou) (2005, 2009).

13.1 Introduction.

13.2 Retrosynthetic Analysis and Strategy Toward 2,2’ –epi-Cytoskyrin A, Rugulosin, and Rugulin, and Rugulin.

13.3 Total Synthesis of 2,2’ –epi-Cytoskyrin A, Rugulosin, and Rugulin.

13.4 Retrosynthetic Analysis and Strategy Toward Antibiotic BE-43472B.

13.5 Total Synthesis of Antibiotic BE-43472B.

13.6 Conclusion.

Chapter 14. Garsubellin A (M. Shibasaki, M. Kanai, S. J. Danishefsky) (2205, 2006).

14.1 Introduction.

14.2 Shibasaki and Kanai’s Retrosynthetic Analysis and Strategy.

14.3 Shibasaki and Kanai’s Total Synthesis.

14.4 Danishefsky’s Retrosynthetic Analysis and Strategy.

14.5 Danishefsky’s Total Synthesis.

14.6 Conclusion.

Chapter 15. Welwitindolinone A (P. S. Baran, J. L. Wood) (2005, 2006).

15.1 Introduction.

15.2 Baran’s Retrosynthetic Analysis and Strategy.

15.3 Baran’s Total Synthesis.

15.4 Wood’s Retrosynthetic Analysis and Strategy.

15.5 Wood’s Total Synthesis.

15.6 Conclusion.

Chapter 16. Iejimalide B (A. Fürstner) (2006, 2007).

16.1 Introduction.

16.2 Retrosynthetic Analysis and Strategy.

16.3 Total Synthesis.

16.4 Conclusion.

Chapter 17. Kedarcidin Chromophore and Maduropeptin Chromophore (A. G. Myers, M. Hirama, M. Inoue, I. Sato) (2007, 2009).

17.1 Introduction.

17.2 Retrosynthetic Analysis and Strategy for Kedarcidin Chromophore.

17.3 Total Synthesis of Kedarcidin Chromophore.

17.4 Retrosynthetic Analysis and Strategy for Maduropeptin Chromophore.

17.5 Total Synthesis of Maduropeptin Chromophore.

17.6 Conclusion.

Chapter 18. Biyouranagin A (K. C. Nicolaou) (2007).

18.1 Introduction.

18.2 Retrosynthetic Analysis and Strategy.

18.3 Total Synthesis.

18.4 Conclusion.

Chapter 19. Azadirachtin (S. V. Ley) (2007, 2009).

19.1 Introduction.

19.2 Retrosynthetic Analysis and Strategy.

19.3 Synthesis.

19.4 Conclusion.

Chapter 20. Resveratro-Derived Natural Products (S. A. Snyder, K. C. Nicolaou, D. Y.-K. Chen) (2007, 2009, 2010).

20.1 Introduction.

20.2 Snyder’s Retrosynthetic Analysis and Strategy for a Collection of Resveratrol-Derived Natural Products.

20.3 Snyder’s Total Synthesis of a Collection of Resveratrol-Derived Natural Products.

20.4 Nicolaou and Chen’s Retrosynthetic Analysis and Strategy for Hopeahainol A and Hopeanol.

20.5 Nicolaou and Chen’s Total Synthesis of Hopeahianol A and Hopeanol.

20.6 Conclusion.

Chapter 21. Chlorosulfolipid Cytotoxin (E. M. Carreira) (2009).

21.1 Introduction.

21.2 Retrosynthetic Analysis and Strategy.

21.3 Total Synthesis.

21.4 Conclusion.

Chapter 22. Sporolide B (K. C. Nicolaou) (2009).

22.1 Inroduction.

22.2 Retrosynthetic Analysis and Strategy.

22.3 Total Synthesis.

22.4 Conclusion.

Chapter 23. 11, 11’ –Dideoxyverticillin A and Chaetocin (M. Movassaghi, M. Sodeoka) (2009, 2010).

  23.1 Introduction.

23.2 Retrosynthetic Analysis and Strategy for 11, 11’ –Dideoxyverticillin A.

23.3 Total Synthesis of 11, 11’ –Dideoxyverticillin A.

23.4 Retrosynthetic Analysis and Strategy for Chaetocin.

23.5 Total Synthesis of Chaetocin.

23.6 Conclusion.

Chapter 24. Vannusal B (K. C. Nicolaou) (2009).

24.1 Introduction.

24.2 Retrosynthetic Analysis and Strategy.

24.3 Total Synthesis.

24.4 Conclusion.

Chapter 25. Haplophytine (T. Fukuyama, H. Tokuyama, K. C. Nicolaou, D.Y. –K. Chen) (2009, 2009).

25.1 Introduction.

25.2 Fukuyama and Tokuyama’s Retrosynthetic Analysis and Strategy.

25.3 Fukuyama and Tokuyama’s Total Synthetis.

25.4 Nicolaou and Chen’s Retrosynthetic Analysis and Strategy.

25.5 Nicolaou and Chen’s Total Synthesis.

25.6 Conclusion.

Chapter 26. Palau’amine (P. S. Baran) (2010).

26.1 Introduction.

26.2 Retrosynthetic Analysis and Strategy.

26.3 Total Synthesis.

26.4 Conclusion.

Image / Photo Credits.

Author Index.

Subject Index.

"Classics in Total Synthesis III will surely itself become a classic in the literature on the state of the art of contemporary organic synthetic chemistry." (Angewandte Chemie, 2011)