Classics in Total Synthesis IIIISBN: 9783527329571
770 pages
March 2011

A wonderful tool for learning and teaching and a musthave for all future and present organic and biochemists.
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 FirstGeneration Retrosynthetic Analysis and Strategy.
6.3 FirstGeneration Total Synthesis.
6.4 SecondGeneration Retrosynthetic Analysis and Strategy.
6.5 SecondGeneration 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 atropAbyssomicin 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 atropAbyssomicin 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’ –epiCytoskyrin A, Rugulosin, and Rugulin, and Rugulin.
13.3 Total Synthesis of 2,2’ –epiCytoskyrin A, Rugulosin, and Rugulin.
13.4 Retrosynthetic Analysis and Strategy Toward Antibiotic BE43472B.
13.5 Total Synthesis of Antibiotic BE43472B.
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. ResveratroDerived 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 ResveratrolDerived Natural Products.
20.3 Snyder’s Total Synthesis of a Collection of ResveratrolDerived 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.
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 postdoctoral fellow in Professor Nicolaou's laboratory.
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