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基本説明
有機化学・生化学専攻の大学院生レベルの超定番テキスト、７年振りの刊行。製薬業界で大きな関心を集める標的分子を収録し、天然物合成の手法について集成。
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. Contents - Chapter 1. Introduction: The Advancing Field of Total Synthesis. Chapter 2. Tetrodotoxin. Chapter 3. Discodermolide. Chapter 4. Azaspiracid – I. Chapter 5. Thiostrepton. Chapter 6. Pentacycloanammoxic Acid Methyl Ester. Chapter 7. Littoralisone, Oseltamivir (Tamiflu), and Hirsutellone B. Chapter 8. Rubicordifolin and Rubiocolin B. Chapter 9. Cyanthiwigins U and F. Chapter 10. Stephacidin B. Chapter 11. Abyssomicin C and atrop-Abyssomicin C. Chapter 12. Tetracycline. Chapter 13. Bisanthraquinone Natural Products. Chapter 14. Garsubellin A. Chapter 15. Welwitindolinone A. Chapter 16. Iejimalide B. Chapter 17. Kedarcidin Chromophore and Maduropeptin Chromophore. Chapter 18. Biyouranagin A. Chapter 19. Azadirachtin. Chapter 20. Resveratro-Derived Natural Products. Chapter 21. Chlorosulfolipid Cytotoxin. Chapter 22. Sporolide B. Chapter 23. 11, 11’ –Dideoxyverticillin A and Chaetocin. Chapter 24. Vannusal B. Chapter 25. Haplophytine. Chapter 26. Palau’amine.
Full Description
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.
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
