Image / Photo Credits 733

Image / Photo Credits

Images of scientists on frontispieces provided by Chapter 5 individuals themselves or from the archives of the authors with use permission granted. Ribbon model of thiostrepton. Courtesy of Dr. Alex Perryman, The Scripps Research Institute.

Chapter 1 Chapter 6 The Parthenon, Acropolis. Credit: Tanya Ronson & Richard Kendrick, (www.worldisround.com/ Candidatus Brocadia anammoxidans (top), articles/325437/photo7.html). Candidatus Kuenenia stuttgartiensis (bottom). Hermes bearing the good person by Praxiteles. Courtesy of Professor Laura van Niftrik, Rad- Archaeological Museum of Olympia. Author: boud University Nijmegen. Ruccoz (http://it.wikipedia.org/wiki/Utente: Roccuz), Creative Commons Attribution-Share Alike 2.5. Chapter 7 Relay runners (Olympic game of Ancient Greece). c Ekdotike Athenon S.A. Publishers. Verbena littoralis. Courtesy of Forest & Kim Starr (www.hear.org/starr).

Chapter 2 Chapter 8 Large pufferfish in Komodo National Park. Author: Nhobgood Nick Hobgood (http://en. Rubia cordifolia. Courtesy of Professor Kevin C. wikipedia.org/wiki/File:Pufferfish_komodo.jpg) Nixon, Cornell University. Creative Commons Attribution-Share Alike 3.0. Dried pufferfish. Courtesy of Professor Justin Du Bois. Chapter 9 Myrmekioderma styx (top: live specimen; Chapter 3 bottom: dried specimen). Courtesy of Professor Andrew J. Phillips, Yale University. Discodermolide crystal. Courtesy of Professor Stuart J. Mickel. Discodermia dissolute sponge. Courtesy of Chapter 10 Dr. John Reed, Harbor Branch Oceanographic Institution, from Johnson Sea-Link Submersible. Aspergillus ochraceus. Author: MWolfin (http:// en.wikipedia.org/wiki/File:Aspergillus_235_ mags_3X3_copy.jpeg) Creative Commons CC0. Chapter 4

Mytilus edulis. c Jon Gross Photography, LCC Chapter 11 (www.jongrossphotography.com). Verrucosisporo strain AB18-032. Courtesy of Professor Hans-Peter Fiedler, Universita¨t Tu¨bin- gen. 734 Image / Photo Credits

Chapter 12 Chapter 19 Streptomyces sp. Courtesy of Dr. David Berd, Azadirachta indica. Credit: William M. Ciesla, Center for Disease Control and Prevention Forest Health Management International, (CDC). Bugowrd.org.

Chapter 13 Chapter 20 Ecteinascidia turbinata, orange. c John Easley Hopea hainanensis. Photography (www.johneasley.com). c LIU Yan (www.PlantPhoto.cn)

Chapter 14 Chapter 21 Garcinia subelliptica. Courtesy of Helen Betts. Mytilus galloprovincialis. c Dr. Luciano Giom- bini (www.lucianogiombini.it).

Chapter 15 Chapter 22 Welwitindolinone A isonitrile synthesis ’End- game’ chalkboard discussion. Courtesy of Pro- Salinispora tropica CNB-392. Courtesy of fessor John L. Wood, Colorado State University. Professor William H. Fenical, Scripps Institution of Oceanography, University of California, San Diego. Chapter 16

Ie Island. Courtesy of Okinawa Convention & Chapter 23 Visitors Bureau, Tourism & Convention PR Department. Sweetings Cay, Grand Bahama. Courtesy of James R. Peters.

Chapter 17 Chapter 24 Actinomadura madurae. Courtesy of Professor Yuzuru Mikami, Chiba University, Research Euplotes vannus. Courtesy of Professor Guella Center for Pathogenic Fungi and Microbial Toxi- Graziano, University of Trento, Italy. coses.

Chapter 25 Chapter 18 Haplophyton cimicidum A. DC. Courtesy of Hypericum chinense L. var. salicifolia.Courtesy Elizabeth Makings, Arizona State University of Takehiko Masuda. Herbarium.

Chapter 26 Palau’s Rock Islands. c iStockphoto.com/ clumpner. Author Index

A Carlough, K. H. 531 F Acton, N. 165 Carreira, E. M. 600ff. Fajans, K. 188f. Aitken, R. A. 197 Carter, R. G. 85f. Fang, J.-M. 234f. Albizati, K. F. 433 Cava, M. P. 690ff. Fattorusso, E. 598 Alder, K. 620 Chen, D. Y.-K. 201, 571, 583ff., Felix, A. M. 27ff. Allred, G. A. 243 691, 706ff. Fenical, W. 294, 617f., 645 Ardisson, J. 60 Chen, M. S. 19f. Fiedler, H.-P. 323, 341 Arefolov, A. 60 Chen, X. 433 Finlay, A. C. 345 Ayers, W. A. 275 Ciamician, G. 526f. Firouzabadi, H. 601 Ciminiello, P. 598 Fiske, P.S. 190 Ciufolini, M. A. 130f. Floss, H. G. 131 B Clive, D. L. J. 469 Forsyth, C. J. 85f. Bagley, M. C. 134 Cong, X. 234 Fu, G. C. 651 Banwell, M. G. 235 Cook, J. M. 27ff. Fujiwara, Y. 23ff. Baran, P.S. 296ff., 435ff., 532f., Co´rdova, A. 204ff. Fukumoto, N. 601f. 722ff. Corey, E. J. 27ff., 162ff., 197f., 222, Fukuyama, T. 234, 433, 691ff. Barbas, C. F., III 188, 203ff. 234, 531f., 669f., 691ff. Fukuyama, Y. 407 Barger, G. 597 Couladouros, E. A. 324ff. Fu¨rstner, A. 451ff. Barton,D.H.R. 18 Crabtree, R. H. 23 Baum, J. S. 210 Curci, R. 220 Bauslaugh, P.G. 527 Curran, D. P. 667f. G Bedford, C. T. 348ff. Gates, J. W. 621 Beecham, A. F. 639 Georgiadis, D. 336 Behenna, D. C. 274 D Gerwick, W. H. 598 Bergman, R. G. 21ff., 484 d’Angelo, J. 700 Ghaffar, T. 299 Berthelot, M. 624 Dakin, H. D. 199 Godel, T. 533f. Betzer, J.-F. 60 Damste´, J.S.S. 162 Goldberg, S. D. 483f. Blechert, S. 625f. Danishefsky, S. J. 202, 411f., 469 Goldman, I. M. 526f. Boger, D. L. 356 Daugulis, O. 25f. Goto, T. 14, 35 Bo¨hnke, H. 133f. Davies, H. M. L. 30ff. Gowland, M. S. 130 Bolm, C. 197 Delpech-Marazano, B. 413 Graves, D. E. 85 Boyd, M. R. 596 Deng, L. 197ff. Gunasekera, S. P. 57 Bredig, G. 188ff. Denmark, S. E. 606f. Breen, J. 377f. Diels, O. 620 Breslow, D. S. 33 Differding, E. 603 H Breslow, R. 18 Dolling, U.-H. 196 Hagedorn, A. A. 351 Broda, E. 161 Domagk, G. 321 Haines, T. H. 598 Buchanan, J. B. 639 Dounay, A. B. 85 Hajos, Z. G. 200f. Bu¨chi, G. 526f. Doyle, M. P. 29ff. Harington, C. R. 597 Buchwald, S. L. 272, 301 Du Bois, J. 15f, 33f. Harrison, S. T. 324, 331ff. Burke, M. D. 272 Dunstan, W. R. 225 Hartwig, J. F. 272 Burreson, B. J. 595 Hasegawa, M. 217 Butterworth, J. H. 545 Hastings, D. J. 528f. Bycroft, B. W. 130 E Hauser, D. 645 Eglinton, G. 498 Hayashi, Y. 234ff. Ellman, J. A. 27f. Helquist, P. 451ff. C Emerson, O. H. 639 Herzon, S. B. 296ff., 310 Cain, P. 202 Enders, D. 205ff., 223f., 235 Hinman, A. 16, 33ff. Calabrese, J. C. 532 Enquist, J. A., Jr. 276ff. Hino, T. 642 Calter, M. A. 194f. Ermer, O. 385f. Hintermann, L. 604 Cao, G. 691f. Evans, D. A. 92, 107ff., 603 Hirama, M. 472ff., 502ff., 596ff. 736 Author Index

Hodges, R. J. 20f. L N Hodgkin, D. C. 131 Lang, R.W. 603 Nagasawa, K. 15 Hopf, H. 169f. Langenbeck, W. 189 Nair, V. 622 Hou, Z. 569f. Lautens, M. 327 Nakagawa, M. 646 Houk, K. N. 201 Lectka, T. 604f. Nakanishi, K. 547 Hudlicky, T. 235 Leet, J. E. 473 Natsume, M. 433 Hunneman, D. H. 223 Lefranc, D. 131 Nelsen, S. F. 532 Lerner, R.A. 188, 203ff. Nicolaou, K. C. 86ff., 134ff., 201, Ley, S.V. 547. 240ff., 330ff., 379ff., 409ff., 481, I Liebeskind, L. S. 243 502ff., 523ff., 535ff., 548f., 571, Inoue, M. 473ff., 502ff. List, H. 188, 203ff., 218f. 583ff., 620ff., 660ff., 691, 706ff. Inoue, Y. 539 Liu, B. 242 Northrup, A. H. 204f. Iranpoor, N. 601 Lu, T.-J. 349 Nugent, W. A. 607 Isaka, M. 238f. Lygo, B. 197 Ishihara, J. 550f. Ishikara, K. 607f. O Isobe, M. 16 M O’Connor, J. M. 620 Itoh, T. 206f. MacGillivray, L. R. 169f. O’Donnell, M. J. 196f. Itokawa, H. 255 MacMillan, D. W. C. 188, 204ff., Oda, J. 197 227ff., 605f. Ohira, S. 622f. Magnus, P. 469 Ohizumi, Y. 225 J Maier, M. E. 336 Okamura, H. 234 Jacobi, P.A. 15 Mandai, T. 235 Okino, T. 598 Jacobsen, E. N. 219f. Mangion, I. K. 227f. Oppolzer, W. 533f. Janowicz, A. H. 21f. Mans, D. M. 203f. Oshitari, T. 235 Johnson, J. A. 23f. Marino, J. P. 691 Ostwald, W. 188, 248 Johnson, J. R. 639 Marshall, J. A. 60ff., 459 Overman, L. E. 33f., 646 Jones, R. R. 484 Martin, H.-D. 166f. Jørgensen, K. A. 212ff., 605f. Mascitti, V. 162ff. Jung, M. E. 210f., 596 Matsunaga, S. 719 P Mayer, J. 483 Padwa, A. 691 Mayer, S. 218f. Pagano, J. F. 127 K Meerwein, H. 27f. Palomo, C. 277 Kagan, H. B. 662 Mehta, G. 167ff. Pan, X.-F. 571 Kametani, T. 313 Meinwald, J. 166 Panek, J. S. 60ff. Kanai, M. 234f., 412ff. Mejı´a-Oneto, J. M. 691 Paone, D. V. 646 Kann, N. 235 Meyer, W. E. 595 Paquette, L. A. 360f., 386 Kashiwada, Y. 541 Meyers, C. Y. 576 Parkins, A.W. 299 Katagiri, K. 645 Mickel, S. J. 57ff. Parrish, D. R. 201 Katz, T. J. 165 Miller, M. A. 164 Pasteur, L. 190 Kawamura, M. 14 Mioduski, J. 166 Paterson, I. 60ff. Kelly, W. L. 133 Mioskowski, C. 596 Pearson, W. H. 203f. Kendall, E. C. 597 Molander, G. A. 664f. Periana, R. A. 21f. Kenny, C. 664f. Moody, C. J. 134 Perrin, C. L. 620 Kerr, M. A. 212, 435 Moore, R. E. 433, 595 Peters, J.-U. 625f. Kilburn, J. D. 667f. Morgan, E. D. 545ff. Pettit, R. 166 Kinsman, A. C. 212, 435 Mosher, H. S. 14 Pfau, M. 700 Kishi,Y. 15f.,35ff.,510,642ff. Movassaghi, M. 646ff. Pfeiffer, M.W. B. 275ff. Kobayashi, J.’i. 449 Mukaiyama, T. 243 Phillips, A. J. 275ff. Kobayashi, S. 473 Murai, A. 550f. Pietra, F. 659 Ko¨ck, M. 719ff. Muratake, H. 433 Plummer, C. C. 689 Kraus, W. 547 Muxfeldt, H. 351f. Poisel, H. 641ff. Kuboki, A. 622f. Myers, A. G. 296ff., 310, 353ff., Porco, J. A. 413 Kumar, S. 622 469ff., 482ff. Porter,A.E.A. 294f. Myles, D. C. 60 Pracejus, H. 190 Prasad, K. 76 Author Index 737

Q Silber, P. 526f. Vanderwal, C. D. 598ff. Qian-Cutrone, J. 293ff. Simpkins, N. S. 412f. Viehe, H. G. 210 Quinn, R. J. 719 Slate, D. L. 598 von Liebig, J. 188f. Sloan, M. F. 33 Vrettou, M. 205ff. Smith, A. B., III 59ff. R Snider, B. B. 324ff. Raistrick, H. 378 Snyder, H. R. 689 W Rastetter, W. H. 645 Snyder, S. A. 571ff., 602f. Wallis, A. F. A. 569 Reddy, T. J. 275 Sodeoka, M. 646ff. Wang, Z. 669f. Regitz, M. 175ff. Somei, M. 309ff. Ward, D. E. 331ff. Repic,O. 76 Sondheimer, F. 483 Wasserman, H. H. 349ff. Reppe, W. 624 Sorensen, E. J. 239ff., 324ff., 338ff. Watanabe, H. 550ff. Roberts, J. D. 18 Srinivasan, R. 531 Weedon, A. C. 527ff. Rodgers, B. I. 620 Staring, E. G. J. 192f. Weindling, R. 639 Roy, A. H. 272 Stoltz, B. M. 274ff. Wenkert, E. 27 Stork, G. 351ff. Wessely, F. 621 Su, T. L. 127 White, M. C. 19f. S SubbaRow, Y. 345 Wiechert, R. 201f. Sames, D. 23f. Su¨ssmuth, R. D. 323f., 341 Williams, R. M. 294ff., 311ff., 645 Sammes, P.G. 294f. Suzuki, K. 223ff. Winkler, J. D. 534 Sanford, M. S. 24f. Witulski, B. 626f. Sarpong, R. 571 Wood, J. L. 435ff. Satake, M. 84ff. T Woodward, R. B. 14, 208ff., 349, Sato, I. 473ff., 502ff. Taber, D. F. 27ff. 639 Sato, K.-I. 16 Tahara, Y. 14 Wulff, G. 133ff. Sato, T. 642 Takaishi, Y. 523f., 541 Wynberg, H. 191ff. Schenck, G. O. 357 Takeya, K. 623 Scheuer, P.J. 719 Takikawa, H. 223ff. Schmidt, U. 641ff. Tanaka, T. 601f. X Schreiber, S. L. 58, 471 Tatsuta, K. 353f. Xiong, Z. 222 Schroeder, D. R. 473 Teles, J. H. 223 Schulman, J. M. 164 ten Hoeve, W. 192 Schwartz, D. A. 691 Thomas, J. M. 18 Y Scott, A. I. 348ff. Thomas, S. O. 595 Yamamoto, T. 622f. Seebach, D. 306f. Togni, A. 604 Yamamoto, Y. 625 Shair, M. D. 201 Tokuyama, H. 691ff. Yao, Z.-J. 234 She, X.-G. 571 Tomasi, A. L. 33f. Yasumoto, T. 15, 84 Sheehan, J. C. 223 Trauner, D. 255ff. Yates, P. 689ff. Shen, Y.-C. 130 Trown, P.W. 640f. Yokoo, A. 14 Shi, Y. 220ff. Trost, B. M. 191f., 235 Yoshimitsu, T. 601f. Shibasaki, M. 234f., 411ff. Tsuda, K. 14 Yu, J.-Q. 26, 272 Shibata, S. 378ff. Shilov, A. E. 19ff. Short, F. W. 225 V Z Sibi, M. P. 217 Vagelos, P.R. 598 Zacharias, D. E. 689 Siegel, D. R. 412ff. Vaillancourt, V. 433 Zou, Y. 330 738 Subject Index Subject Index

A – oxidation 20 aminoacyl–transfer RNA (tRNA) 347 abyssomicin alkaloids 225f. p-aminobenzoic acid (PABA) 322 – biology and chemistry 338 – cinchona 190ff. amnesic shellfish poisoning (ASP) abyssomicin B – cyclotryptamine 645 83 – biosynthesis 323 – epidithiodiketopiperazine 639ff. ampelopsin D 571ff. abyssomicin C 321ff., 337, 617 – hapalindole-type 433 – retrosynthetic analysis 572 – retrosynthetic analysis 324ff. – indole 225, 294 – total synthesis 577 – total synthesis 329ff. – oroidin 719ff. ampelopsin F 569ff. atrop-abyssomicin C 321ff., 337ff., – pyrrole–imidazole 719 – total synthesis 578 617 alkanes 17 amythiamicin D 130 – total synthesis 331 alkene anammoxosome membrane 162 iso-abyssomicin C 329 – olefin cross-metathesis reaction angelic acid derivative 144 abyssomicin D 340 214 anhydrochlortetracycline 348ff. – biomimetic synthesis 340 a-alkoxysulfone anhydrotetracycline 349, 371 – biosynthesis 323 – cyclic 107, 121 4,9-anhydrotetrodotoxin 16 iso-abyssomicin D 341 alkyl iodide 97 aniline system 697 acetaldehyde 188 alkylation anthradihydroquinone 389 a-acetoxyketone 40 – enantioselective 196 anthraquinones 255 acetylene 624 [2+2+2] alkyne trimerization 620 anti-HIV agent 407 acetylide–aldehyde cyclization 482f., allocyathins 275 antibiotic 504 l-allose 204ff. – bisanthraquinone 377 – chelation controlled 511 allyl enol carbonate – broad-spectrum 321, 345 acetylide–aldehyde ring closure 511 – Tsuji allylation 274 – b-lactam 291 acetylide–pyridinium coupling 481 allyl ester cleavage 152 – tetracycline 346f. Achromycinr 346 allylation – thiopeptide 127ff. actinomycetes – stereoablative and enantioselective antibody–drug conjugate 471 –marine 617 double 282f. anticancer agent 58 – terrestrial 617 allylic alcohol 110 antidepressant 407 N-acyliminium species 219f. allylic hydroperoxide 357 antifeedant 409, 545f. Adams catalyst 173 altohyrtin C 107 antiostatin A1 626 aflatoxin B1 292 Alzheimer’s disease 407 – total synthesis 626f. aglycone 473f. Amberlyst-15 558 antitumor – protected 502 ambiguine 433 – agent 293 aiphanol 622 ambiguine H 435 – antibiotics 471 – total synthesis 623 amide – antibody 471 l-alanine 144 – tertiary 45 aplydactone 162f. alcohol amide bond formation arctigenin 29ff. – allylic 110 – anomalous 143 – total synthesis 29ff. – homopropargylic 112 amine aromadendranediol 214 – secondary 119 – secondary 199 – total synthesis 214 aldehyde amino acid aryl hydrazine 699 – a,b-unsaturated 74 – enantioselective synthesis 197 aryl tosylate 272 – Brown allylation 101 – organocatalytic synthesis 198 – quinine-derived 272 aldol condensation 235 a-amino acid 196 arylation 25 aldol reaction 199 b-amino acid arylselenocyanide 683 – asymmetric 194 –protected 487 aspergamide B 293f. – asymmetric intramolecular 214 d-amino acid derivative 196 aspidophytine 690ff. – enantioselective 203 l-amino acid derivative 197 asteriscanolide 360 – titanium-mediated 677 4-amino-4-deoxychorismate (ADC) – total synthesis 361 aliphatic C–H bond –lyase 323 atorvastatin 292 – functionalization 16 –synthase 323 atropisomerism 338, 502 Subject Index 739

Aureomycinr 345 benzoin reaction Candidatus Kuenenia stuttgartien- avrainvillamide 293ff. – enantioselective 223f. sis 162 – retrosynthetic analysis 303 3-benzyloxyisoxazole system 351f. canthinone 690ff. – total synthesis 310 Bergman cycloaromatization 475 canthiphytine 690ff. ent-avrainvillamide 296ff., 311 bicyclo[2.2.2]diazaoctane ring carbon–carbon bond-forming reaction – dimerization 303 system 294 –SmI2-mediated 662 – retrosynthetic analysis 296f., 311 bicyclo[2.2.2]octane ring system carbonylation – total synthesis 302 277 – Pd-catalyzed 442 axinellamine A 720ff. bicyclo[3.3.1]nonane core 408f. carboxylation axinellamines 722 (S)-BINOL 333 – cyclohexane 23 aza-Diels–Alder cycloaddition 131 bis-b-ketoester 283 carpanone 255 aza-Diels–Alder dimerization 133ff. bisanthraquinone natural product (R)-carvone 435 – biomimetic 142 377 caryophyllene 531 aza-Mannich cyclization Bischler–Napieralski cyclization – total synthesis 532 – stereoselective 141 695 cassigarol B 571ff. aza-Mannich reaction 134 biyouyanagin 208 – retrosynthetic analysis 573 2-azaadamantane N-oxyl (AZADO) biyouyanagin A 523ff., 535ff. – total synthesis 582 681 –24-epi-biyouyanagin A 540 catalyst azadirachtin 545ff. –24(R)-biyouyanagin A 535 – universal asymmetric 203 – biosynthesis 553 –24(S)-biyouyanagin A 536 cerium(IV) ammonium nitrate – retrosynthetic analysis 553f. – retrosynthetic analysis 535 (CAN) 166,218,259ff. azadirex 546 – total synthesis 540 chaetocin 639ff. azaspiracid shellfish poisoning l-N-Boc-phenylselenoalanine 149 – retrosynthetic analysis 651ff. (AZP) 83 boronic acid 271 – total synthesis 653ff. azaspiracid-1 83ff. boronic ester 301, 706ff. chirality – retrosynthetic analysis 92ff. brasoside 225ff. – Seebach’s method for self-repro- – total synthesis 95ff. – retrosynthetic analysis 227 duction 306 ent-azaspiracid-1 107f., 121f. – total synthesis 228 chlorination azaspiro system 104 bromination 172, 182 – methane 22 Azatinr 546 – radical 151 a-chlorination 605f. – reductive 173 (+)-B-chlorodiisopinocamphenyl- B bromoform 595 borane 75 B23 296 bromoketalization 549 a-chloroketone 725 bacteria Brown allylation chlorosulfolipid 595ff. – Gram-positive 130 – aldehyde 102, 388, 456 chlorosulfolipid cytotoxin 595ff. Baeyer–Villiger oxidation 36ff., 383 bryostatin 2 107 – retrosynthetic analysis 609 Barbier reaction 662f. Burgess reagent 151, 308 – total synthesis 609ff. Barton allylic oxidation 419 butadiene 36 chlortetracycline 345ff., 596 Barton ester 179f. Chugaev elimination 681 Barton etherification 243 C cinchona alkaloids 190f. Barton remote functionalization 17 C–H bond cinchonidine 190 Barton–McCombie deoxygenation – functionalization 16f. cinchonine 190 248, 561, 713 – oxidation 20 (R)-citronellal 242, 535ff. Bauslaugh–Schuster–Weedon me- – Pt-mediated activation 24 (S)-citronellal 536f. chanism 527 – regioselective C–H arylation 25f. (S)-citronellol 228 BE-43472A 377ff. calicheamicin 469 CJ-17,665 294 I BE-43472B 377ff. calicheamicin g1 469ff., 597 Claisen condensation 175, 283, 710 – retrosynthetic analysis 394 calicheamicinone 469ff. Claisen rearrangement 301ff., – total synthesis 395ff. calmodulin inhibitor 596 555ff., 678 Beckmann rearrangement 36 camphor 603 clusianone 407ff., 425ff. BEMP (2-t-butylimino-2-diethyl- – (+)-camphor 189, 278 – (+)-clusianone 413 amino-1,3-dimethylperhydro-1,3,2- camphorcarboxylic acid 187 7-epi-clusianone 409 diazaphosphorine) resin 604 – (–)-camphorcarboxylic acid 188f. cobalt benzocyclobutene 363ff. – (+)-camphorcarboxylic acid 189 – Co-doped aluminum phosphate – derivative 370 – decarboxylation 189 molecular sieve (CoAlPO-18) 18 benzodioxane 622ff. Candidatus Brocadia anammoxi- –Co(PPh3)3Cl-mediated reductive benzoic acid 364 dans 162 dimerization 646 (R)-benzoin 223 ent-cocaine 203f. – total synthesis 204 740 Subject Index colombiasin A 30ff. – radical 484, 549ff. (e)-12a-deoxyanhydrotetracycline – total synthesis 32 – Se-promoted 425 351ff. Colvin rearrangement 489 –SmI2-promoted 444 deoxyrubroskyrin 377 Comins reagent 104, 537 – transannular 483, 498, 722 6-deoxytetracycline 353ff. Comins–Brown metallation 490f. – transannular radical 476 – analogues 355 conjugate addition [2+2] cycloaddition 169ff., 225ff. (e)-12a-deoxytetracycline 353 – Kharasch condition 675 –asymmetric 181 7-deprenylgarsubellin A 411ff. conjugate reduction – photoinduced 231, 526ff. – retrosynthetic analysis 413 – l-Selectride-promoted 442 [2+2+2] cycloaddition Dess–Martin oxidation 97f., 119ff., convergent fragment coupling 61 – transition metal-catalyzed 624ff. 230, 243ff., 301, 328, 361, 444, Cope rearrangement 30f., 621 cyclobutadiene 511, 538 copper –Fe(CO)3-complexed 166ff. Dess–Martin periodinane 76 – Cu(I) thiophene-2-carboxylate cyclobutene 167ff. desymmetrization (CuTC) 243, 462 cyclohexane – cyclic anhydrides 197ff. –salt 27 – carboxylation 23ff. – organocatalytic 199 Corey–Chaykovsky reaction 369 – insertion 46 Dewar benzene 166 Corey–Fuchs alkynylation – nitrene insertion 33 (DHQD)2-PHAL 146, 190, 630 – aldehyde 490, 509 cyclohexane derivative 2,6-di-t-butyl-4-methylphenol coriolin 667 – stable twist-boat 191 (BHT) 353 coronary heart disease (CHD) 567 cyclohexane system 236 di-O-methyldynemicin A methyl Cp*RuCl(cod) 625ff. cyclohexanone system 413ff. ester 471 m-CPBA (meta-chloroperbenzoic cyclohexenes 216, 235 diarrhetic shellfish poisoning acid) 39ff. cyclooctatetraene 172 (DSP) 83, 598 Crabtree catalyst 116 cyclooctene system 361 [2.2.2]diazabicyclooctane system cross-metathesis 311 cyclopentadiene 620f. 312 cubane 164 cyclopentene system 694ff. a-diazoester 30 a-cuparenone 29f. cyclopentenone 181 a-diazoketone 47, 175ff. – total synthesis 30 cyclosporin A 58, 291 diazomethane Curtius rearrangement 235 cyclotrimerization 624ff. – photolysis 28 cyanogen cyclotryptamine DIBAL-H 46 – hydration 188 – oligomeric 645 dibromoolefin 488 cyanohydrin 190 cyclotryptamine alkaloid 645 dibromophakellin 596 cyanthiwigin AC 275 cytoskyrin A 377ff. dichlorination cyanthiwigin F 271ff. 2,2l-epi-cytoskyrin A 256, 377ff. – enantioselective 603 – retrosynthetic analysis 281 – retrosynthetic analysis 381f. 11,11l-dideoxyverticillin A 639ff. – total synthesis 286 – total synthesis 384ff. – retrosynthetic analysis 647 cyanthiwigin U 271ff. cytoskyrin cascade 382ff. – total synthesis 648ff. – retrosynthetic analysis 276 Dieckmann condensation 283, – total synthesis 277 D 331ff., 351, 494 cyanthiwigin W 275 DABCO 305 Diels–Alder adduct cyanthiwigin Z 275 danicalipin A 598ff. – intermolecular 212 cyanthiwigins 271ff. – biosynthesis 599 Diels–Alder cycloaddition 36ff., cyathane 274f. Danishefsky diene 555 168, 210, 234ff., 277, 328, 349ff., cyathins 275 Darzens-type reaction 69 622, 724 cyclic anhydride 197ff. DBU (1,8-diazabicyclo[5.4.0]undec- – intramolecular 212, 261 cyclic carbamate 49, 440ff. 7-ene) 180, 229, 444, 495 – singlet oxygen 349ff. cyclization de Mayo reaction 533 – thermal 330, 533 – acid-induced 575 Dean–Stark trap 398 Diels–Alder dimerization 38, 168 – cationic 571ff. decalin 547 Diels–Alder oligomerization 167 –6-endo-trig 550 cis-decalin system 36ff. Diels–Alder reaction 294 –8-endo-trig 665 dehydrogliotoxin 645 – asymmetric 277, 333 –5-exo-dig radical 668 dehydropiperidine 130ff. – intramolecular 324ff. –4-exo-trig 670 – retrosynthetic analysis 139 – organocatalytic 211f. –5-exo-trig 550, 569ff., 667ff., 714 dehydropyran system 558 Diels–Alder regioselectivity 396 –6-exo-trig 552, 665 (e)-6-demethyl-6-deoxytetra- Diels–Alder synthesis 166 –7-exo-trig 576ff. cycline 349 diethyl-i-propylsilyl chloride –5-exo-trig ketyl–olefin 667 demethylsalvicanol 623 (DEIPSCl) 494 –6-exo-trig ketyl–olefin 669 diethylaminosulfur trifluoride – Lewis acid-promoted 92ff. (DAST) 148, 495 Subject Index 741 dihydroanthraquinone 379ff. enyne metathesis cascade 625 furomollugin 259ff. – retrosynthetic analysis 383 epidithiodiketopiperazine alkaloid ent-dihydrocorynantheol 206f. 639ff. G – total synthesis 207 epidithiodiketopiperazine system garsubellin A 407ff. (R)-2,3-dihydrofarnesal 218f. 640ff. –(e)-garsubellin A 412ff. dihydropyran 117 epothilone B 58 – retrosynthetic analysis 414ff. p-dihydroquinone 38 epoxidation – total synthesis 411f., 423ff. dihydroxylation – enantioselective 220f. GE2270A 130 – Kishi model 510 epoxide opening 244, 330ff. geminal effect 359 diketone – Lewis acid-catalyzed 607 gemtuzumab ozogamicin 471 – cyclic 191 – Lewis base-catalyzed 606 geranylgeranyl pyrophosphate 275 diketopiperazine system 642ff. erinacines 275 Ghaffar platinum catalyst 299 diketopiperizine system 294 erythromycin A 208ff. Gif oxidation 18 dimerization – total synthesis 208 glabrescol 223f. –Co(PPh3)3Cl-mediated reductive d-erythronic acid 45 – total synthesis 222 646 l-erythrose derivative 204f. Glaser coupling 483 diol esperamicin 469 Glaser oxidative coupling – l-tartaric acid-derived 101 esperamicin A1 479 – Eglinton conditions 498 dioxirane 220f. ester gliotoxin 639ff. dipyridine polyene 170 – a,b-unsaturated 227ff. l-glucose 204 diradical trapping 528f. esterification 604 d-glucose derivative 228ff. dirhodium catalyst 29ff. estrone 202 glycosylation 231, 485ff., 500ff. discodermolide 57ff. – total synthesis 202 – b-selective 228 – retrosynthetic analysis 61 Evans–Saksena reduction 76, 444, glycylcyclines 346 – total synthesis 77f. 633 glyoxylate ene reaction dispiroketal system 85 extensively drug-resistant (XTR) – enantioselective 111f. dithiane 97f. strain 238 graciliformin 377 ditryptophenaline 646 Gram-negative bacteria 127, 321, – total synthesis 646 F 345 divergent synthesis 63ff. Felkin–Anh Gram-positive bacteria 127ff., 321, 1,5-diyn-3-ene system 499 – attack 508 345 diyne 626 – control 47 gramine system 313 DNA damage 475 – transition state 99 grandione 623 dodecahedrane 385 Fenton reagent 18f. – biomimetic synthesis 623 doxycycline 346ff. Fischer indole synthesis 692ff. Gribble reduction 309 dynemicin A 469ff. fischerindole 433 Grubbs I olefin metathesis catalyst 12-epi-fischerindole G 435ff. 625 E 12-epi-fischerindole I 435ff. Grubbs I olefin metathesis initiator ecteinascidin 743 197f. Fisher esterification 282, 327, 493 361, 388 1,2-elimination FK506 58 Grubbs II metathesis initiator 214, – reductive 504ff. flavoskyrin 377ff. 264, 425 –SmI2-mediated 514 a-fluorination Grubbs II olefin metathesis catalyst elisapterosin B 30ff. – enantioselective 604 337 – total synthesis 32 flustramine B 212f. Grubbs II ruthenium carbene Ellman’s reagent 641 – total synthesis 213 initiator 278 enamine 199 folic acid 321f. Grubbs–Hoveyda II catalyst 109 – catalysis 199 FR182877 58 Grubbs–Hoveyda II olefin metathesis enamine–iminium cascade 209 French paradox 567 catalyst 314, 419 endo Diels–Alder cycloaddition 277 Friedel–Crafts acylation 459 enediyne 469ff. Friedel–Crafts alkylation 308ff. H enol ether 39f. – intramolecular 436, 585ff. Hajos–Parrish ketone 201 b-enolamide – transannular 572ff. haloalkanes 595 – masked 353ff. Friedel–Crafts disconnection 311 halogenation method enolate coupling l-fructose 222 –asymmetric 9,595 – oxidative 303 fructose derivative 220 – enantioselective 603ff. enone 353ff., 383ff., 557 fugu 13 a-halogenation – (+)-camphor-derived 277 functionalization – enantioselective 605 enone–olefin cycloaddition 527 – aliphatic C–H bond 16f. halomon 596ff. 742 Subject Index

– total synthesis 601 hispidospermidin 33 influenza virus 232f. Hantzsch ester 218 – total synthesis 34 ingenol Hantzsch thiazole synthesis 139ff. homodimerization – total synthesis 534 hapalindole A 433 – reductive 648ff. intersystem crossing (ISC) 527 hapalindole B 433 homopropargylic alcohol 108f. iodocarbocyclization hapalindole G 434 hopeahainol A 571, 583ff. – electrophilic 421ff. hapalindole H 433 – retrosynthetic analysis 583 iodocyclization hapalindole J 433 – total synthesis 585ff. – enantioselective 607f. hapalindole M 433 hopeanol 571, 583ff. Ireland–Claisen rearrangement 550f. hapalindole O 433 – retrosynthetic analysis 583 iridoid system 228ff. hapalindole Q 212, 433ff. – total synthesis 585ff. iridoids 225 – total synthesis 212 Horner–Wadsworth–Emmons d-isoascorbic acid 45 hapalindole U 433 coupling 96 isochrysohermidin 356 haplophytine 689ff. – Masamune–Roush variant 96, 230 isoschizandrin – retrosynthetic analysis 691ff., Horner–Wadsworth–Emmons – total synthesis 665 706ff. olefination 234 – total synthesis 695ff., 705ff. – aldehyde 491 J harmicine 219f. Horner–Wadsworth–Emmons Jacobsen chromium catalyst 505 – total synthesis 220 reaction 457, 574 Johnson–Lemieux oxidative cleavage HATU (2-(7-aza-1H-benzotriazole- human immunodeficiency virus – olefin 266, 459 1-yl)-1,1,3,3-tetramethyluronium (HIV) 523 Jørgensen asymmetric epoxidation hexafluorophosphate) 148ff., 313 hyalodendrin 645 242f. Hauser annulation 353, 383ff. hydrazine 162ff. juglone 395 Heck coupling hydrazone 702 juglone derivative 395ff. – regiocontrolled oxidative 272 hydrogen–deuterium exchange Heck reaction 458 reaction 20f. K Heck-type cyclization hydrostannation (R,R)-Katsuki manganese salen – Ni-mediated 548 – regio- and stereocontrolled 455f. complex 151 Heck-type reaction hydroxyacetone 204 Keck radical allylation – Pd-mediated 315 a-hydroxyester 585 – iodide 429 – reductive 484, 499, 548 b-hydroxyketone 63 kedarcidin 473 hetero-Diels–Alder cycloaddition – Evans–Saksena reduction 444, 633 kedarcidin chromophore 469ff., 172, 206, 555, 622 hyperforin 407 499ff. hetero-Diels–Alder reaction ent-hyperforin 413 – retrosynthetic analysis 483ff. – biomimetic 258ff. hyperolactone C 523ff., 535ff. – total synthesis 487ff. – enantioselective 117, 556ff. hypnophilin 667 kedarcidin chromophore aglycone – intramolecular 256ff., 633 486 hetero-ene reaction I ketene trap – enantioselective 505f. IBX oxidation 337f., 388 –asymmetric 190 a-heteroarylation reaction 218 iejimalide A 449ff. ketene–olefin [2+2] cycloaddition hexacycle 308ff. iejimalide B 449ff. – antarafacial 440 hexafluoroisopropanol (HFIP) 298f., – retrosynthetic analysis 451ff. a-ketocarboxylate 132 665 – total synthesis 453ff. a-ketoester 585 hexamethyldisilylazine (HMDS) iejimalide C 449ff. b-ketoester 283, 604 675 iejimalide D 449ff. – enantioselective a-fluorination l-hexose 204f. – total synthesis 463 604 hexoses 230 imidazolidinone catalyst 211ff., 605 ketyl–olefin cyclization highly active antiretroviral therapy iminium 201 –SmI2-mediated 285, 662 (HAART) 523 – catalysis 201ff. ketyl–olefin reaction 663 hirsutellone A 238ff. iminium Diels–Alder reaction 210f. Koga enantioselective alkylation hirsutellone B 187ff., 237ff. – asymmetric variant 210 415 – retrosynthetic analysis 240f. – enantioselective variant 211 KS-504d 596 – total synthesis 242ff. iminium reduction 712 Kugelrohr distillation 621 hirsutellone C 238ff. immunosuppressant 58, 130, 291 hirsutellone D 238f. indacrinone 196 L hirsutellone E 238f. indole alkaloids 225, 294 L11 protein 130 hirsutellone F 238ff. indolenine system 692ff. b-lactam antibiotics 291 hirsutic acid C 191 indoline system 709 lactone 584f. – total synthesis 192 Subject Index 743

– a-oxygenation 334 manganese(III)-mediated oxidative – transannular 341 b-lactone 194 radical cyclization 678 micrococcin P1 127ff. lactonization 256 Mannich reaction microtubule-stabilizing agent 58 ladderane 162ff. – organocatalytic 205 minimum inhibitory concentration – [3]ladderane 164ff., 178ff. Mannich-type reaction 313 (MIC) 130 – [4]ladderane 166 l-mannose 204 minocycline (Minocinr) 346ff. – [5]ladderane 169ff. Margosan-Or 546 Mitsunobu reaction 366, 490, 673 – [8]ladderane 169 marine actinomycetes 617f. mixed-lymphocyte reaction (MLR) – [11]ladderane 169 Markovnikov attack 600 assay 57 – [13]ladderane 168 Martin sulfurane 417, 444, 673 modhephene 27 – [n]ladderane 164 Masamune–Roush variant 96 – total synthesis 29 ladderane lipid 182 – Horner–Wadsworth–Emmons mollugin 262ff. large group nonbonding effect 359 coupling 96, 230 monocyclic polyprenylated acyl- Lawesson’s reagent 140 Masamune–Sharpless synthesis 204 phloroglucinol (MPAP) 409f. Lindlar reduction 110 massadine chloride 720ff. monoterpenes 225 Lipitorr (atorvastatin) 292 massadines 723 Montmorillonite K-10 436 lithiation 388, 625 Meerwein salt 313 Mukaiyama aldol reaction 119, 204 lithium 4,4l-di-t-butylbiphenyl Meerwein–Ponndorf–Verley – stereocontrolled 230 (LiDBB) radical anion 113, 334 reduction 39 Mukaiyama aldol-like reaction 676 lithium–halogen exchange 72, 97, menthol ester 145 Mukaiyama-type vinylogous aldol 118, 484, 506ff. mesitylenesulfonyl chloride 700 reaction lithospermic acid 27 mesityllithium 209 – enantioselective 115 – total synthesis 28 mesylation 223 multidrug-resistant (MDR) strain lithotrophs 161 metallo-[2+2] cycloaddition 238 littoralisone 187f., 225ff. – intramolecular 337 Mycobacterium tuberculosis 237 – retrosynthetic analysis 227 metallonitrenoid 32 Mylotargr (gemtuzumab ozogami- – total synthesis 228ff. methacrolein 314 cin) 471 loganin 225f. methane lomaiviticins A and B 617 – chlorination 22 N – mechanism of action 619 – oxidation 21 N1999A2 471ff., 487 longifolene methanol naphthodihydroquinones 255ff. – total synthesis 533 – synthesis 22 naphthoic acid 490ff. lovastatin 291 methicillin-resistant Staphylococcus naphthoquinone derivative 262ff. low density lipoprotein (LDL) 291 aureus (MRSA) 127, 323 naphthoquinone system 262 Luche reduction 557ff., 629f. l-methionine 132 ent-napyradiomycin A1 602 9-methoxy-9-borabicyclononane – total synthesis 603 M (9-MeO-BBN) 73 Narasaka–Prasad reduction 76 macro-palau’amine 722ff. para-methoxybenzyl (PMB) NeemAzal Fr 546 macrocycle 154, 336 trichloroacetimidate 66 Neemixr 546 macrocyclic olefin 241ff. methyl l-mycaroside 495 Negishi coupling 281 macrolactam 513f. methyl vinyl ketone 201, 535ff. – Pd-mediated 72 macrolactamization 153ff., 504 methyl xanthate formation 713 Negishi cross coupling maduropeptin 473 2-methyl-6-nitrobenzoic anhydride – Pd-mediated 284 maduropeptin chromophore 473ff., (MNBA) 452, 490 nemorosone 407, 425ff. 516ff. 4-methyl-o-quinone 621 – total synthesis 425 – retrosynthetic analysis 502ff. N-methyliminodiacetic acid (MIDA) neocarzinostatin 471 – total synthesis 505 boronates 272 neocarzinostatin chromophore maduropeptin chromophore Michael addition 191ff., 209ff., 230 471ff. aglycone 514f. –asymmetric 191 – total synthesis 482 magnesium monoperoxyphthalate – chiral auxiliary-controlled asym- neocarzinostatin protein–chromo- hexahydrate (MMPP) 561 metric 700 phore complex 472 malhamensilipin A 598ff. – Dieckmann condensation cascade nerve growth factor (NGF) 225 (R)-malic acid 193 353, 383 neuraminidase (NA) 232 – total synthesis 193 – enantioselective 214 neuraminidase inhibitor 232 (S)-malic acid 193f., 537f. – intermolecular 391 neurotoxic shellfish poisoning – total synthesis 193 – intramolecular 228, 341, 379ff., (NSP) 83 Mander’s reagent 245 539 neurotrophic factor 407 – radical 457 nicotine 188 – stereoselective 355 744 Subject Index nimbidin 552 a-oxygenation 217, 228 pinacol-type rearrangement nitrene 32 – lactone 334 – oxidative 294 – insertion into cyclohexane 33 oxytetracycline 345ff. – oxidative, ring-contracting 435 o-nitrobenzenesulfonylhydrazine ozonolysis 724 Pinnick oxidation 121, 230, 266, (NBSH) 366 514 NO38 296 P Plasmodium falciparum 130 Norrish type I reaction paeonilactone B 667 platensimycin 665 – photoinduced 552 – total synthesis 668 – total synthesis 666 19-norsteroids 201 palau’amine 719ff. poly-cyclobutane 162 notoamide A 293 – retrosynthetic analysis 722f. polycyclic polyprenylated acyl- notoamide B 293f. – total synthesis 725ff. phloroglucinol (PPAP) 408ff. ent-notoamide B 316 palladium catalysis 272ff. polyketide 57ff., 478ff. – total synthesis 317 – Pd(0) catalyst 283, 423, 459 polyoxamic acid 205ff. Noyori asymmetric reduction 459, pallidol 571ff. – total synthesis 207 695 – retrosynthetic analysis 573 polyphenolic natural product 567 Noyori catalyst 460 – total synthesis 579 potassium trifluoroborates 271f. Nozaki–Hiyama–Kishi coupling 73, [2.2]paracyclophane 169 PPTS (pyridinium p-toluene sulfo- 99 paraffins 17 nate) 66 NPM1.1 296 paralytic shellfish poisoning (PSP) PPY ((R)-(+)-4-pyrrolidinopyridinyl nuclear Overhauser enhancement 83 (pentamethylcyclopentadienyl)- (NOE) 90, 540 Parikh–Doering oxidation 67ff., iron) 651 nucleocidin 595f. 110ff. presporolide 471, 619 nucleophilic activation 475 Parkins’ platinum catalyst 299 prismane 164 nucleophosmin (numatrin) 296 Paterson boron aldol reaction 63, – total synthesis 165 75ff., 103, 119 d-proline 209, 230, 306 O paucifloral F 571ff. l-proline 201ff., 230, 306ff. olefin cross-metathesis 108, 214, – total synthesis 575 promothiocin A 134 264 penicillin 291 prontosil 321 olefin metathesis 234 penicillin G 291 propargylic mesylate 555ff. Oppolzer addition 367 penicillin ring system 27 – retrosynthetic analysis 556 – enantioselective 367 penitrem D 668 prostaglandin G2 (PGG2)methyl organocatalysis 187ff., 217 pentachlorophenyl ester 605 ester 669f. organocatalytic synthesis 198ff., 236 pentacycle 314 psycholeine 646 organometallic species 19ff. pentacycloanammoxic acid methyl pterodactyladiene 166f. organopalladium species 25 ester 161ff., 533 – total synthesis 167 oroidin 719 – retrosynthetic analysis 171ff. pufferfish 13ff. oroidin alkaloid 719ff. – total synthesis 172ff. py2AgMnO4-promoted oxidation ortho lithiation 388, 423 pentamethylated hemsleyanol E 580 649 oseltamivir (Tamiflur) 187f., 232ff. pentamethylpiperidine 197 pyrrole–imidazole alkaloid 719 – retrosynthetic analysis 235 pentaprismane 164 pyrrole–imidazole coupling 720 – total synthesis 236f. Peterson elimination 73 pyrrolidine system 306 oxabicyclo[2.2.2]octane ring phase-transfer catalysis 196f. system 324 –asymmetric 196 Q – tetronate-fused 331ff. 4-phenyl-pyridine N-oxide 151 quadrangularin A 569ff. oxamide 188 l-phenylalanine 202ff. – total synthesis 570 oxazole 130 N-(phenylseleno)phthalimide quagrigemine C 646 oxidation (N-PSP) 410 quercetin 624 – asymmetric a-oxidation 228 phosphonoacetate derivative 236 quinaldic acid 132ff., 149ff. – directed C–H oxidation 25 p p p* photoactivation of enone quinic acid 233 – methane 21 527 quinidine 190ff. –py2AgMnO4-promoted 649 [2+2] photocycloaddition 165ff., quinine 190ff. oxidative cleavage 178ff., 227, 526ff. quinoline 481 – Johnson–Lemieux protocol 459 photooxidation o-quinone Diels–Alder cyclo- oxidative dimerization – sensitizer 358 addition 620ff. – terminal alkyne 485 phthalide anion 353, 383 o-quinone methide 258ff. oxidative radical cyclization Pictet–Spengler-type reaction p-quinone methide 576ff. – Mn(III)-mediated 676 – enantioselective 219f. o-quinonedimethide 362ff. Oxoner 220ff., 580 – enzymatic 225 pinacol reaction 663f. Subject Index 745

R rugulin 377ff. – dye-sensitized photochemical for- radical initiator V-70 653 – retrosynthetic analysis 381f. mation 357 radical–olefin reaction 663f. – total synthesis 384ff. singlet oxygen Diels–Alder cycload- radical–polar crossover reaction rugulosin 377ff. dition 356 –SmI2-promoted 668 – retrosynthetic analysis 381f. singlet oxygen ene reaction 357ff. radicalisin 378f. – (–)-rugulosin 379f. – regioselectivity 359 Ramberg–Ba¨cklund olefination 167, – (+)-rugulosin 379 siomycin A 130 243ff., 572ff. – total synthesis 393ff. siphonarienal 194f. rapamycin 58 Rule of Fives 531 – total synthesis 195 reactive oxygen species (ROS) 640 ruthenium SN2 displacement 365, 608, 727 [3,3]-rearrangement 703 – carbene 278 SN2 reaction Red-Alr 99 – complex 285, 696 – intramolecular 369 r Red-Al analog 483 SN2l cyclization 314f. r Red-Al -mediated reduction 68 S SN2l displacement redox cycling 640 Saegusa–Ito oxidation – intramolecular 365 1,2-reduction –Pd(OAc)2-mediated 298 SN2l reaction 312, 475 – Luche condition 557 Sakurai-type allylation 262ff. – intramolecular 477 – selective 557 salannin 552 – radical 298 reductive homodimerization 647ff. salinosporamide A 617 SNAr reaction 398 Reformatsky reaction 663f. – mechanism of action 619 solanapyrone D 211f. Relenzarr 233 samarium diiodide 285, 444f., 514, Sommelet–Hauser process 365 Reppe reaction 625 662f. Sonogashira coupling 485, 505ff., resveratrol 567ff. saponification 492 628 resveratrol-derived natural product sappanone B 223ff. – chemoselective 496 568 – total synthesis 225 Sonogashira-type cross-coupling – retrosynthetic analysis 571ff. sarcodonins 275 – carbonylative 539 – total synthesis 574 saxitoxin 14f. l-sorbose 222 retro-Friedel–Crafts reaction 569 scabronines 275 spiro tetronic acid cyclohexene retro-Michael addition 237 sceptrin 532f. motif 325 rhazinilam – total synthesis 532 spongistatin 2 107 – enantioselective total synthesis 24 Schenck ene reaction 357 sporidesmin A 645 rhodium Schwartz reagent 70 sporolide 471 – Rh carbenoid 29ff. secododecahedrane 385f. sporolide A 618ff. – Rh nitrenoid C–H oxidation 34, secologanin 225 – biosynthesis 619 43ff. Seebach’s method sporolide B 617ff. –Rh2(4S-MPPIM)4 29 – self-reproduction of chirality 306 – biosynthesis 619 ring-closing metathesis 277f., 336, Selectfluorr 604 – retrosynthetic analysis 627f. 388, 461ff. K-Selectride 76 – total synthesis 629ff. ring-opening–ring-closing olefin L-Selectride 105, 341 statin 291f. metathesis cascade 277f. semi-pinacol rearrangement 439ff. Staudinger reduction 153 RNA sensitizer 358 stephacidin A 293f., 306ff. – 16S ribosomal (rRNA) 162, 347 – photooxidation 358 – biomimetic total synthesis 295 – 23S ribosomal (rRNA) 130 Shapiro reaction 670ff. –(e)-stephacidin A 294 – transfer (tRNA) 130, 347 Sharpless asymmetric dihydroxyla- – total synthesis #309 Robinson annulation tion 144, 190, 417ff. ent-stephacidin A 311ff. – catalyst-controlled asymmetric – chemoselective 248 – total synthesis 316 535 Sharpless asymmetric epoxidation stephacidin B 291ff., 304ff. Rovis catalyst 223 506 – retrosynthetic analysis 304 Rubia Shiina esterification 497 – total synthesis 305ff. – cordifolia 255 Shiina macrolactonization 452f. ent-stephacidin B 296ff., 311ff. – oncotricha 255 shikimic acid 233f. – retrosynthetic analysis 296f., 311 rubicordifolin 255ff. sialic acid 232 – total synthesis 298ff., 312ff. – retrosynthetic analysis 258 [2,3]-sigmatropic rearrangement Still–Gennari olefination 74, 459 – total synthesis 259f. – ylide 365 Stille cross-coupling 92, 105, 419, rubioncolin A 255ff. [3,3]-sigmatropic rearrangement 622 462 rubioncolin B 255ff. silver picolinate 728 Stork–Zhao olefination 242 – retrosynthetic analysis 262f. silyl enol ether 204 Strecker reaction – total synthesis 262ff. singlet oxygen 356f. – stereoselective 146 rubroskyrin 377 Strecker-like addition 300 746 Subject Index strictosidine 227 – total synthesis 37ff. vinyl triflate 105 strychnine 225 thiamine 223 vitamin B1 223 stylissadine A 719f. (e)-6-thiatetracycline 351 vitamin B9 321 styloguanidine 720 thiazole 130f., 147 styrene maleic acid neocarzinostatin thiazolidine system 138 W (SMANCS, zinostatin stimala- thiazoline–thiazole system 149 Wacker oxidation 119 mer) 471 4,4l-thiobis-(6-t-butyl-3-methyl- Wacker-type oxidative cyclization sulfanilamide 321 phenol) 40 413ff. sulfolane 308f. thioglycoside 495 Wagner–Meerwein-type 1,2-shift sulfonamides 321 thiopeptide antibiotics 127ff. – intramolecular 309, 436 sulfone–aldehyde coupling reaction thiostrepton 127ff. warfarin 212 121 – retrosynthetic analysis 135ff. –(R)-warfarin 212f. Super-Hydrider 538 – total synthesis 138ff. Weinreb amide 61ff., 102ff., 194, Suzuki coupling 271f., 297ff., 462, l-threonine derivative 147 333 706ff. l-thyroxine 597 welwitindolinone 433 –sp3–sp2 73 tigecycline (Tygacilr)346 welwitindolinone A (welwitindoli- Suzuki cross-coupling 272 titanium carbine 49 none A isonitrile) 433ff. Suzuki reaction 675 titanium complex – (+)-welwitindolinone A 439 Swern oxidation 96ff., 121, 175, – TADDOL-based 604 –(e)-welwitindolinone A 440ff. 278, 328, 388, 490 trabectidin 198 – retrosynthetic analysis 435f. transition metal-catalyzed [2+2+2] – total synthesis 435ff. T cycloaddition 624ff. Wieland–Miescher ketone 200ff. T4 hormone 597 transmetallation 459ff. Wilkinson’s catalyst 626ff. Takai methylenation 48 2,4,6-trichlorobenzoic acid 451 WIN 64821 646 Takai–Utimoto olefination 458, trifurylphosphine (TFP) 105 ent-WIN 64821 646 608ff. triplet oxygen 356 Wittig Tamao–Fleming oxidation 383ff. tryptamine 219ff. – homologation 243 Tamiflur 187ff., 232ff. l-tryptophan 132 – methylenation 98, 532 – retrosynthetic analysis 235 Tsuji allylation – olefination 176, 609f. – total synthesis 236f. – allyl enol carbonate 274 Wolff rearrangement 175ff. tarichatoxin 14 – enantioselective 274 Wurtz coupling tartaric acid 190 tuberculosis (TB) 237 – transannular 426 TAS-F (tris(dimethylamino)sulfonium tylosin (Tylanr)495 difluorotrimethylsilicate) 266, Y 452f. U Yamaguchi acetylide–pyridinium Taxolr 58f.,202,292 Ullmann coupling 301 coupling 481 TEMPO (2,2,6,6-tetramethylpiperi- uncialamycin 471ff. Yamaguchi esterification 151 dine-1-oxyl) 66ff., 217, 307 – total synthesis 481f. Yamaguchi macrolactonization 156, – oxidation 369 451 Terramycinr 345 V ylide terrestrial actinomycetes 617 V-70 radical initiator 653 – [2,3]-sigmatropic rearrangement tetracycline 345ff. vanadium catalyst 335 365 – asymmetric total synthesis 354 vancomycin 596 Yondelisr 198 – retrosynthetic analysis 362 vancomycin-intermediate Staphylo- ytterbium diiodide 662 –(e)-tetracycline 351 coccus aureus (VISA) 323 – total synthesis 364ff. vannusal A 659f., 685 Z tetraene 222 vannusal B 659ff. zanamivir (Relenzarr)233 tetrahydro-b-carboline system – retrosynthetic analysis 670ff. Zhao olefination 63ff. 692ff., 706 – total synthesis 672ff. ent-zingiberene 523ff., 536ff. tetrahydrofolic acid 323 verticillin A 645 ent-7-epi-zingiberene 523ff., 535ff. – biosynthesis 322 Vibramycinr 346 zinostatin stimalamer 471 tetrahydrothiophenes 214f. Vilsmeier reagent 230 tetraol 647ff. Vilsmeier–Haack tetraphenylporphine (TPP) 349ff. – cyclization 706ff. tetrodamine 35ff. – formylation 695 – masked 36ff. – reagent 695 tetrodotoxin 13ff., 35ff., 52 vinyl iodide 99 – retrosynthetic analysis 35ff. vinyl stannane 92ff., 104f.