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Classics in Total Synthesis III: Further Targets, Strategies, Methods

ISBN: 978-3-527-32957-1
770 pages
March 2011
Classics in Total Synthesis III: Further Targets, Strategies, Methods (3527329579) cover image


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

Adopting his didactically skillful approach, K.C. Nicolaou compiles in this textbook the important synthetic methods that lead to a complex molecule with valuable properties. He explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections and contrasting these to other synthetic methods.
A wonderful tool for learning and teaching and a must-have for all future and present organic and biochemists.
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Table of Contents

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.

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Author Information

K.C. Nicolaou holds joint appointments at The Scripps Research Institute, where he is the Chairman of the Department of Chemistry and holds the Darlene Shiley Chair in Chemistry and the Aline W. and L.S. Skaggs Professorship of Chemical Biology, and the University of California, San Diego, where he is Distinguished Professor of Chemistry. His impact on chemistry, biology and medicine flows from his research works in chemical synthesis and chemical biology described in numerous publications and patens. For his contributions to science and education, he was elected Fellow of the New York Academy of Sciences, Fellow of the American Academy of Arts and Sciences, Member of the National Academy of Sciences, USA, Member of the German Academy of Sciences Leopoldina, and Corresponding Member of the Academy of Athens, Greece. He is the recipient of many prizes, awards and honors.

Jason S. Chen received his A.B. and A.M. degrees in Chemistry from Harvard University in 2001. After two years as a medicinal chemist at Enanta Pharmaceuticals, he began graduate studies at The Scripps Research Institute under the guidance of Professor K.C. Nicolaou. He received a National Defense Science and Engineering Graduate fellowship, and completed his Ph.D. studies in 2008. He currently is a post-doctoral fellow in Professor Nicolaou's laboratory.
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"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)
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 Read the press announcement: Our author K.C. Nicolaou has earned three prestigious international honors recently, including the Nemitsas Prize 2014 in Chemistry.

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