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.

Table of Contents:
Chapter 1 Introduction: The Advancing Field of Total Synthesis 1.1 Targets 2 1.2 Strategies and Methods 2 1.3 Classics in Total Synthesis III 10 Chapter 2 Tetrodotoxin Y. Kishi; J. Du Bois (1972; 2003) 2.1 Introduction 13 2.1.1 Aliphatic C–H Bond Functionalization 16 2.2 Kishi’s Retrosynthetic Analysis and Strategy 35 2.3 Kishi’s Total Synthesis 37 2.4 Du Bois’ Retrosynthetic Analysis and Strategy 43 2.5 Du Bois’ Total Synthesis 45 2.6 Conclusion 52 Chapter 3 Discodermolide Novartis: S. J. Mickel; I. Paterson; A. B. Smith, III (2004) 3.1 Introduction 57 3.2 Retrosynthetic Analysis and Strategy 61 3.3 Total synthesis 65 3.3.1 Synthesis of the Common Precursor 65 3.3.2 Divergent Synthesis of the Fragments 67 3.3.3 Fragment Coupling and Completion of the Synthesis 72 3.4 Conclusion 79 Chapter 4 Azaspiracid-1 K. C. Nicolaou; D. A. Evans (2004, 2006; 2007) 4.1 Introduction 83 4.2 Nicolaou’s Retrosynthetic Analysis and Strategy 92 4.3 Nicolaou’s Total Synthesis 95 4.3.1 Synthesis of the ABCDE Ring System 95 4.3.2 Synthesis of the FHI Ring System 101 4.3.3 Fragment Coupling and Completion of the Synthesis 105 4.4 Evans’ Retrosynthetic Analysis and Strategy 107 4.5 Evans’ Total Synthesis 108 4.5.1 Synthesis of the ABCD Ring System 108 4.5.2 Synthesis of the EFGHI Ring System 115 4.5.3 Fragment Coupling and Completion of the Synthesis 121 4.6 Conclusion 121 Chapter 5 Thiostrepton K. C. Nicolaou (2004) 5.1 Introduction 127 5.2 Retrosynthetic Analysis and Strategy 135 5.3 Total Synthesis 138 5.3.1 Synthesis of the Dehydropiperidine Fragment 138 5.3.2 Synthesis of the Other Fragments 144 5.3.3 Fragment Coupling and Completion of the Synthesis 152 5.4 Conclusion 156 Chapter 6 Pentacycloanammoxic Acid Methyl Ester E. J. Corey (2004, 2006) 6.1 Introduction 161 6.1.1 Synthesis of Ladderane Compounds 164 6.2 First-Generation Retrosynthetic Analysis and Strategy 171 6.3 First-Generation Total Synthesis 172 6.4 Second-Generation Retrosynthetic Analysis and Strategy 177 6.5 Second-Generation Total Synthesis 179 6.6 Conclusion 182 Chapter 7 Littoralisone, Oseltamivir (Tamiflur), and Hirsutellone B D. W. C. MacMillan; Y. Hayashi; K. C. Nicolaou (2005; 2009; 2009) 7.1 Introduction 187 7.1.1 Catalysis by Cinchona Alkaloids 190 7.1.2 Enamine Catalysis 199 7.1.3 Iminium Catalysis and Enamine–Iminium Cascades 209 7.1.4 Other Examples of Organocatalysis 217 7.2 Introduction to Littoralisone 225 7.2.1 Retrosynthetic Analysis of Littoralisone 227 7.3 Total Synthesis of Littoralisone 228 7.4 Introduction to Oseltamivir (Tamiflur) 232 7.4.1 Retrosynthetic Analysis of Oseltamivir (Tamiflur) 235 7.5 Total Synthesis of Oseltamivir (Tamiflur) 236 7.6 Introduction to Hirsutellone B 237 7.6.1 Retrosynthetic Analysis of Hirsutellone B 240 7.7 Total Synthesis of Hirsutellone B 242 7.8 Conclusion 248 Chapter 8 Rubicordifolin and Rubioncolin B D. Trauner (2005, 2008) 8.1 Introduction 255 8.2 Retrosynthetic Analysis of Rubicordifolin 258 8.3 Total Synthesis of Rubicordifolin 259 8.4 Retrosynthetic Analysis of Rubioncolin B 262 8.5 Total Synthesis of Rubioncolin B 262 8.6 Conclusion 266 Chapter 9 Cyanthiwigins U and F A. J. Phillips; B. M. Stoltz (2005; 2008) 9.1 Introduction 271 9.2 Phillips’ Retrosynthetic Analysis and Strategy 276 9.3 Phillips’ Total Synthesis 277 9.4 Stoltz’ Retrosynthetic Analysis and Strategy 281 9.5 Stoltz’ Total Synthesis 282 9.6 Conclusion 286 Chapter 10 Stephacidin B A. G. Myers; P. S. Baran; R. M. Williams (2005; 2005; 2007) 10.1 Introduction 291 10.2 Myers’ Retrosynthetic Analysis and Strategy 296 10.3 Myers’ Total Synthesis 298 10.4 Baran’s Retrosynthetic Analysis and Strategy 303 10.5 Baran’s Total Synthesis 305 10.6 Williams’ Retrosynthetic Analysis and Strategy 311 10.7 Williams’ Total Synthesis 312 10.8 Conclusion 317 Chapter 11 Abyssomicin C and atrop-Abyssomicin C E. J. Sorensen; K. C. Nicolaou (2005; 2006) 11.1 Introduction 321 11.2 Sorensen’s Retrosynthetic Analysis and Strategy 324 11.3 Sorensen’s Total Synthesis of Abyssomicin c 327 11.4 Nicolaou’s Retrosynthetic Analysis and Strategy 331 11.5 Nicolaou’s Total Synthesis of Abyssomicin c and atrop-Abyssomicin c 331 11.5.1 Chemistry and Biology of the Abyssomicins 338 11.6 Conclusion 342 Chapter 12 Tetracycline A. G. Myers (2005, 2007) 12.1 Introduction 345 12.1.1 Singlet Oxygen Ene Reactions 356 12.2 Retrosynthetic Analysis and Strategy 361 12.3 Total Synthesis 364 12.4 Conclusion 373 Chapter 13 Bisanthraquinone Natural Products K. C. Nicolaou (2005, 2009) 13.1 Introduction 377 13.2 Retrosynthetic Analysis and Strategy Toward 2,2l-epi-Cytoskyrin A, Rugulosin, and Rugulin 381 13.3 Total Synthesis of 2,2l-epi-Cytoskyrin A, Rugulosin, and Rugulin 384 13.4 Retrosynthetic Analysis and Strategy Toward Antibiotic BE-43472B 394 13.5 Total Synthesis of Antibiotic BE-43472B 395 13.6 Conclusion 402 Chapter 14 Garsubellin A M. Shibasaki, M. Kanai; S. J. Danishefsky (2005; 2006) 14.1 Introduction 407 14.2 Shibasaki and Kanai’s Retrosynthetic Analysis and Strategy 413 14.3 Shibasaki and Kanai’s Total Synthesis 413 14.4 Danishefsky’s Retrosynthetic Analysis and Strategy 421 14.5 Danishefsky’s Total Synthesis 423 14.6 Conclusion 429 Chapter 15 Welwitindolinone A P. S. Baran; J. L. Wood (2005; 2006) 15.1 Introduction 433 15.2 Baran’s Retrosynthetic Analysis and Strategy 435 15.3 Baran’s Total Synthesis 435 15.4 Wood’s Retrosynthetic Analysis and Strategy 440 15.5 Wood’s Total Synthesis 440 15.6 Conclusion 446 Chapter 16 Iejimalide B A. Fürstner (2006, 2007) 16.1 Introduction 449 16.2 Retrosynthetic Analysis and Strategy 451 16.3 Total Synthesis 454 16.3.1 Synthesis of the Fragments 454 16.3.2 Fragment Coupling and Completion of the Synthesis 462 16.3.3 Alternative Synthetic Approach 464 16.4 Conclusion 466 Chapter 17 Kedarcidin Chromophore and Maduropeptin Chromophore A. G. Myers; M. Hirama, M. Inoue, I. Sato (2007; 2009) 17.1 Introduction 469 17.2 Retrosynthetic Analysis and Strategy for Kedarcidin Chromophore 483 17.3 Total Synthesis of Kedarcidin Chromophore 487 17.3.1 Synthesis of the Fragments 487 17.3.2 Fragment Coupling and Completion of the Synthesis 496 17.4 Retrosynthetic Analysis and Strategy for Maduropeptin Chromophore 502 17.5 Total Synthesis of Maduropeptin Chromophore 505 17.5.1 Synthesis of the Fragments 505 17.5.2 Fragment Coupling and Completion of the Synthesis 511 17.6 Conclusion 518 Chapter 18 Biyouyanagin A K. C. Nicolaou (2007) 18.1 Introduction 523 18.1.1 Photoinduced [2þ2] Cycloadditions 526 18.2 Retrosynthetic Analysis and Strategy 535 18.3 Total Synthesis 537 18.4 Conclusion 541 Chapter 19 Azadirachtin S. V. Ley (2007, 2009) 19.1 Introduction 545 19.1.1 Selected Strategies for the Construction of the Congested C8–C14 Bond 547 19.2 Retrosynthetic Analysis and Strategy 553 19.3 Synthesis 555 19.4 Conclusion 562 Chapter 20 Resveratrol-Derived Natural Products S. A. Snyder; K. C. Nicolaou, D. Y.-K. Chen (2007, 2009; 2009, 2010) 20.1 Introduction 567 20.2 Snyder’s Retrosynthetic Analysis and Strategy for a Collection of Resveratrol-Derived Natural Products 571 20.3 Snyder’s Total Synthesis of a Collection of Resveratrol-Derived Natural Products 574 20.4 Nicolaou and Chen’s Retrosynthetic Analysis and Strategy for Hopeahainol A and Hopeanol 583 20.5 Nicolaou and Chen’s Total Synthesis of Hopeahainol A and Hopeanol 585 20.6 Conclusion 592 Chapter 21 Chlorosulfolipid Cytotoxin E. M. Carreira (2009) 21.1 Introduction 595 21.1.1 Asymmetric Halogenation Reactions 600 21.2 Retrosynthetic Analysis and Strategy 608 21.3 Total Synthesis 609 21.4 Conclusion 612 Chapter 22 Sporolide B K. C. Nicolaou (2009) 22.1 Introduction 617 22.1.1 o-Quinone Diels–Alder Cycloadditions 620 22.1.2 Transition Metal-Catalyzed [2þ2þ2] Cycloadditions 624 22.2 Retrosynthetic Analysis and Strategy 627 22.3 Total Synthesis 629 22.4 Conclusion 635 Chapter 23 11,11’-Dideoxyverticillin A and Chaetocin M. Movassaghi; M. Sodeoka (2009; 2010) 23.1 Introduction 639 23.2 Retrosynthetic Analysis and Strategy for 11,11l-Dideoxyverticillin A 646 23.3 Total Synthesis of 11,11l-Dideoxyverticillin A 648 23.4 Retrosynthetic Analysis and Strategy for Chaetocin 651 23.5 Total Synthesis of Chaetocin 653 23.6 Conclusion 655 Chapter 24 Vannusal B K. C. Nicolaou (2009) 24.1 Introduction 659 24.1.1 SmI 2 -Mediated Ketyl–Olefin Cyclization 662 24.2 Retrosynthetic Analysis and Strategy 670 24.3 Total Synthesis 672 24.3.1 Synthesis of the Left Domain 672 24.3.2 Synthesis of the Right Domain 675 24.3.3 Fragment Coupling, Completion of the Synthesis, and Structural Reassignment 678 Chapter 25 Haplophytine T. Fukuyama, H. Tokuyama; K. C. Nicolaou, D.Y.-K. Chen (2009; 2009) 25.1 Introduction 689 25.2 Fukuyama and Tokuyama’s Retrosynthetic Analysis and Strategy 691 25.3 Fukuyama and Tokuyama’s Total Synthesis 695 25.3.1 Synthesis of the Left Domain 695 25.3.2 Synthesis of the Right Domain 700 25.3.3 Fragment Coupling and Completion of the Synthesis 702 25.4 Nicolaou and Chen’s Retrosynthetic Analysis and Strategy 706 25.5 Nicolaou and Chen’s Total Synthesis 706 25.5.1 Synthesis of the Left Domain 706 25.5.2 Synthesis of the Right Domain 708 25.5.3 Fragment Coupling and Completion of the Synthesis 711 25.6 Conclusion 716 Chapter 26 Palau’amine P. S. Baran (2010) 26.1 Introduction 719 26.2 Retrosynthetic Analysis and Strategy 722 26.3 Total Synthesis 725 26.4 Conclusion 730 Image / Photo Credits 733 Author Index 735 Subject Index 738