List of Abbreviations

Ac acetyl acac acetylacetonate AcOH acetic acid AIBN 2,2’-azobis(2-methylpropionitrile) AMP adenosine monophosphate cAMP cyclic adenosine monophosphate ADP adenosine diphosphate ATP adenosine triphosphate 9-BBN 9-borabicyclo[3.3.1]nonane BINAP 2,2’-bis(diphenylphosphano)-1,1’-binaphthyl BINOL 2,2’-dihydroxy-1,1‘-binaphthyl Bn benzyl Boc N-t-butoxycarbonyl Boc2O di-t-butyl dicarbonate Bu n-butyl sBu sec.-butyl tBu t-butyl Bu2BOTf di-n-butylboryl trifluoromethanesulfonate BuOH n-butanol tBuOH t-butanol Bz benzoyl CAN ceric ammonium nitrate CBS reduction Corey-Bakshi-Shibata reduction Cbz carbobenzyloxy protecting group CoA coenzyme A CSA campher-10-sulfonic acid DABCO 1,4-diazabicyclo[2.2.2]octane dba dibenzylideneacetone DBN 1,5-diazabicyclo[4.3.0]non-5-ene DBS dibenzosuberyl DBU 1,8-diazabicyclo[5.4.0]undec-7-ene DCC dicyclohexylcarbodiimide DCE 1,2-dichloroethane DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone DEAD diethyl azodicarboxylate DHP dihydropyrane DIAD diisopropyl azodicarboxylate

B. Schaefer, Natural Products in the Chemical Industry, DOI 10.1007/978-3-642-54461-3, © Springer-Verlag Berlin Heidelberg 2014 790 List of Abbreviations

DIBAlH diisobutylaluminium hydride DIC diisopropylcarbodiimide DIGLYME bis(2-methoxyethyl) ether DIPEA N,N-diisopropylethylamine DMAP 4-dimethylaminopyridine DME 1,2-dimethoxyethane DMF dimethylformamide DMSO dimethylsulfoxide EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Et ethyl EtOH ethanol FAD flavin adenine dinucleotide Hex n-hexyl cHex cyclohexyl HMG 3-hydroxy-3-methylglutaryl HMPT, HMPA hexamethylphosphoric triamide HOMO highest occupied molecular orbital IC50 concentration of a substance that is required for 50% inhibition ICI Imperial Chemical Industries LD50 lethal dose, where 50% of test subjects exposed would die LDA lithium diisopropylamide LUMO lowest unoccupied molecular orbital MCPBA m-chloroperbenzoic acid Me methyl MeOH methanol Mes, mesylate methanesulfonate MTBE t-butylmethylether NAD nicotinamide adenine dinucleotide NaHMDS sodium bis(trimethylsilyl)amide NBS N-bromosuccinimide NCS N-chlorosuccinimide NMO N-methylmorpholine-N-oxide NMP N-methyl-2-pyrrolidone PCC pyridinium chlorochromate PEA 1-phenylethylamine PEG polyethylene glycol Ph phenyl PLE pig esterase PPA 1-propanephosphonic acid cyclic anhydride* Pr n-propyl iPr iso-propyl PrOH n-propanol iPrOH isopropanol PTC phase-transfer catalysis py pyridine List of Abbreviations 791

Ra-Ni Raney nickel Red-Al sodium bis(2-methoxyethoxy)aluminium hydride SAME S-adenosylmethionine TBAF tetra-n-butylammonium fluoride TBS t-butyldimethylsilyl TEMPO 2,2,6,6-tetramethylpiperidine-1-oxyl Tf trifluoromethanesulfonyl TFA trifluoroacetic acid THF tetrahydrofurane THP tetrahydropyrane TIPSOTf triisopropylsilyl trifluoromethanesulfonate TMEDA tetramethylethylenediamine TMSOiPr isopropoxy trimethylsilane TMSOTf trimethylsilyl trifluoromethanesulfonate Tos, tosylate 4-toluenesulfonate TPAP tetra-n-propylammonium perruthenate TPP triphenylphosphane TPPO triphenylphosphane oxide Triflate trifluoromethanesulfonate Trityl triphenylmethyl TsOH, pTSA p-toluenesulfonic acid

*: unless otherwise indicated Directory of Illustrations

0. Preface 0.1 Public domain, USDA photo by Scott Bauer.

1. Indroduction 1.1 Wikipedia: Conscious, 1.2 NASA, 1.3 Public domain, 1.3 Public domain, 1.4 BASF, 1.5 BASF, 1.6 BASF, 1.7 Public domain, 1.8 Public domain.

2. Colourants 2.2 BASF, 2.4 Chrumps, 2.4 Public domain, 2.5 Dorothe Jacobs, Textilmuseum Neumünster, 2.6 Public domain, 2.7 BASF, 2.7 Kurt Stüber, 2.7 Alupus, 2.8 Lynn Downey, Levi Strauss & Co.San Francisco, 2.8 Lynn Downey, Levi Strauss & Co. San Francisco, 2.9 BASF, 2.10 Dr. Ansgar Schäfer, BASF, 2.11 Public domain, 2.12 BASF, 2.13 Prof. Dr. Roland Melzer, Universität München, 2.14 Fæ, 2.15 Public domain, 2.17 BASF, 2.17 H. Zell, 2.18 Public domain, 2.19 Public domain, 2.20 Thomas Seilnacht, 2.20 Public domain, 2.21 Petr Kratochvil, pub- lic domain, 2.23 Steve Evans aka “babasteve”, 2.24 Khayman.

3. Fragrances and Flavourings 3.1 Anselm Schafer, 3.1 Prof. Steve Kleene, University of Cincinnati, 3.3 Fuqiang Xu, Wuhan, China, 3.5 BASF, 3.6 Pressestelle MÄURER & WIRTZ, Martina Drewing PR, Beauty *Fashion* Lifestyle Düsseldorf, 3.8 Claudia Hermanns-­ Heber, Guerlain, 3.9 BASF, 3.10 Robert Seidel, The Essential Oil Company, 3.11 BASF, 3.13 Fritz Geller-Grimm, 3.15 Claudia Hermanns-Heber, Guerlain, 3.17 BASF, 3.19 Javier martin, 3.25 Michael Becker, 3.26 Simon Eugster- Simon, 3.29 Walkerma, 3.30 Feureau, 3.31 Public domain, 3.32 Die Rheinpfalz, IWZ, 3.33 Die Rheinpfalz, IWZ, 3.33 Glane23, 3.35 Symrise, Holzminden, 3.37 SHISEIDO Deutschland GmbH, Düsseldorf, 3.38 Dr. André Schüle, Zoo- logischen Garten Berlin, 3.39 Daderot, 3.39 Николай Усик / http://paradoxu- sik.livejournal.com/, 3.40 Public domain, 3.41 Francisco Manuel Blanco (O.S.A.), 3.41 Kat from St Albans, United Kingdom, 3.42 Public domain, Ferdi- nand Bauer, 3.43 Public domain, 3.44 Public domain, 3.45 Claudia Her- manns-Heber, Guerlain, 3.45 Pressestelle MÄURER & WIRTZ, Martina Drewing PR, Beauty *Fashion* Lifestyle, Düsseldorf, 3.46 Scott Portelli, Wildlife Photographer, Sydney, 3.46 Peter Kaminski, 3.47 C. Allemann, 3.50 Carsten Niehaus, 3.50 Andrea Buratti, 3.51 Kurt Stueber, 3.52 United States Fish and Wildlife Service, 3.53 M. Rohde, HZI, Braunschweig, Germany, 3.54 Georg E. Schulz, Freiburg, 3.55 Georg E. Schulz, Freiburg, 3.57 Maurice Perry, 3.58 arz,

B. Schaefer, Natural Products in the Chemical Industry, DOI 10.1007/978-3-642-54461-3, © Springer-Verlag Berlin Heidelberg 2014 794 Directory of Illustrations

3.58 Antje Brüne, Kosmetikverband Wuppertal, 3.58 Ina Patschicke, COTY RESTIGE, Mainz, 3.58 Ines Karpa, Clarins GmbH, Starnberg.

4. Amino acids 4.1 R. Hadian, U.S. Geological Survey, Public domain, 4.2 YassineMrabet, GFDL, CC-BY-SA license, 4.3 NASA, public domain, 4.4 Public domain, 4.7 BASF, 4.8 www.atomium.be - SABAM Belgium 2012, 4.9 BASF, 4.12 Public domain, 4.14 Dr. Andrea Hohmeyer, Evonik Industries AG, Konzernarchiv, 4.15 Dr. Andrea Hohmeyer, Evonik Industries AG, Konzernarchiv, 4.17 Dr. Lothar Eggeling, Forschungszentrum Jülich, 4.20 Jeremiah, 4.20 Public domain, 4.21 Clark R. Landis, University of Wisconsin-Madison, 4.22 Symrise, Holz- minden, 4.23 Public domain, 4.24 Symrise, Holzminden.

5. Pharmaceuticals 5.4 Fernando Tatagiba, 5.6 Public domain, 5.8 Public domain, 5.17 Prof. K. Ravi Acharya, University of Bath, 5.20 The Third Man, London Film Productions, André Mieles, Deutsches Filminstitut-DIF e.V., 5.22 Wikidi, 5.23 Public do- main, 5.24 Public domain Nobel foundation, 5.25 Konrad Soyez, Universität Potsdam, 5.26 Dr. Birgit Hoff, BASF SE, 5.27 Mrjohncummings, Science Mu- seum London / Science and Society Picture Library, 5.28 Prof. Dr. Alessandro Riva, Università di Cagliari, 5.28 Dr. Birgit Hoff, BASF SE, 5.29 Public domain Nobel foundation, 5.34 Public domain Nobel foundation, 5.30 Public domain, 5.35 Rizzoli Editore, Milano, 5.36 Public domain, 5.37 Zbigniew Bela, Museum of Pharmacy in Kraków, 5.38 Public domain, 5.39 Public domain, 5.41 Prof. Dr. Henry I. Mosberg, University of Michigan, Ann Arbor, 5.45 Public domain, 5.48 BASF, 5.48 BASF, 5.48 Christian Pagenkopf, 5.50 Public domain, 5.51 Pu- blic domain, 5.52 Prof. Dr. Dr. M. H. Zenk, Universität München, 5.54 Peter Jolly, Tasmanian Alkaloids Pty Ltd, 5.54 Peter Jolly, Tasmanian Alkaloids Pty Ltd, 5.55 Public domain, 5.56 Public domain, 5.57 Public domain, 5.58 Public domain, 5.59 Public domain, 5.61 Staff Sergeant Angelita Lawrence US Air Force Public Affairs, Public domain, 5.63 Dr. Michel De Waard, Grenoble In­ stitut des Neurosciences, 5.64 Barbetorte, 5.67 en:User:Tzahy, 5.70 Willow, 5.71 Christian Fischer, 5.72 Public domain, 5.72 Public domain, 5.73 Bayer AG: Corporate History & Archives, 5.74 Bayer AG: Corporate History & Archives, 5.75 Bayer AG: Corporate History & Archives, 5.76 Bayer AG: Corporate His- tory & Archives, 5.77 Bayer AG: Corporate History & Archives, 5.78 Prof. Dr. R. Michael Garavito, Michigan State University, Dr. Guenter Trummlitz, Boehringer-Ingelheim, 5.79 Mababole, 5.79 PD-USGOV, 5.81 Public domain, 5.82 Bernd Brägelmann Braegel Mit freundlicher Genehmigung von Dr. Martin Steinhoff, 5.83 Public domain, 5.84 Prof. Dr. R. Michael Garavito, Michigan State University, 5.86 Prof. Dr. R. Michael Garavito, Michigan State University, 5.87 Dr. Ravi G. Kurumbail, , New York, 5.88 Prof. Dr. R. Michael Garavi- to, Michigan State University, 5.90 Dr. Garret A. FitzGerald, Institute for Trans- lational Medicine and Therapeutics, Philadelphia, 5.91 Klewic, 5.92 Selket, 5.93 Monopol, 5.94 Susanne Uebele, Archiv der Max-Planck-Gesellschaft, Berlin-Dahlem, 5.95 Elf Sternberg, derivative work: Tsaitgaist, 5.96 Nephron, 5.97 Prof. Dr. R. Michael Garavito, Michigan State University, 5.97 Prof. Dr. R. Directory of Illustrations 795

Michael Garavito, Michigan State University, 5.99 Gary Williams, California Academy of Sciences, 5.100 Public domain, 5.103 Public domain, 5.104 Public domain, 5.107 Jeff Servoss, Public domain, 5.108 Rong-Yang Wu, Institute of Botany, Academia Sinica, Taipei, Taiwan, 5.110 Dr. Ansgar Schäfer, BASF, 5.110 Boghog, 5.113 James Heilman, MD, 5.114 Jeff Dahl, Public domain, 5.115 Public domain, 5.116 Public domain, 5.118 Alex_brollo, 5.119 Holger Motzkau, Stockholm, 5.120 Max-Planck-Institut für Biochemie, 5.121 Erich Nigg, Max-Planck-Institut für Biochemie, 5.122 Michael Linnenbach, 5.123 Kenneth Downing awrence Berkeley National Laboratory UC Berkeley, 5.124 Harold P. Erickson, Duke University Medical Center, Durham, 5.125 Eva Nogales, Howard Hughes Medical Institute, Berkeley, 5.126 ArtMechanic, 5.127 Emgaol, 5.127 Walter Siegmund, 5.131 Dr. Gilbert Gorr, Phyton Biotech GmbH, 5.131 Dr. Gilbert Gorr, Phyton Biotech GmbH, 5.134 Public domain, 5.135 Melitta Franceschini, South Tyrol Museum of Archaeology, Bolzano, 5.136 Public domain, 5.137 Public domain, 5.138 Hugo Vogel public domain, 5.139 Novogen, 5.140 Public domain, 5.140 Public domain, 5.141 Maseltov, Eva Lynen, 5.141 Public domain, Peter Geymayer, 5.142 Prof. Dr. Igor E. Konstan- tinov, University of Melbourne, Melbourne, 5.143 Michael Park, MD, Iowa Heart Center, West Des Moines, 5.144 Bob Sanders, UC Berkeley, 5.145 HYBRID MEDICAL ANIMATION / SPL / AGENTUR FOCUS, 5.146 Dr. Sabine Bern- schneider-Reif, Merck, Darmstadt, 5.147 Prof. Dr. Juergen R. Schaefer, Univer- sitätsklinikum Giessen und Marburg, 5.148 Dr. Sabine Bernschneider-Reif, Merck, Darmstadt, 5.149 Pieria, Public domain, 5.150 Science and Technology Foundation of Japan, 5.151 Public domain, 5.155 Prof. Dr. Johann Deisenhofer, The University of Texas Southwestern Medical Center, D­ allas, 5.157 Public ­domain, 5.158 Public domain, 5.161 Public domain, 5.162 WHO, 5.163 Didier Desouens, 5.164 David and Noelle Soren, University of Arizona, Tucson, [email protected], 5.164 Il Dottore, 5.165 Public domain, 5.166 Public domain, 5.167 Public domain, 5.168 Public domain, 5.169 Public domain, 5.170 Public domain, 5.170 Public domain, 5.171 Public domain, 5.172 Public domain, 5.173 Public domain, 5.174 Matthias Giger Hefenhofen, Schweiz, 5.175 Image by Ute Frevert; false color by Margaret Shear, 5.175 Public domain, 5.175 Nephron, 5.176 Ernst Hempelmann, 5.176 David Sullivan, JHU Bloomberg School of Public Health, 5.176 Iwona Tesarowicz, 5.177 Public do- main, 5.177 Public domain, 5.177 H. Zell, 5.178 Public domain, 5.179 Public domain, 5.180 Public domain, 5.180 Boissonas, 5.180 Public domain, 5.181 Dr Katherine de Villiers-Chen, Stellenbosch University, South Africa, 5.183 Public domain, 5.184 Wollschaf, 5.185 Public domain, 5.186 Alfred Krauth (1879- 1939), Public domain, 5.187 Otis Historical Archives of “National Museum of Health & Medicine”, 5.189 Public domain, 5.189 Public domain, 5.190 Jorge Ferreira, 5.191 E. Kehnel, 5.192 Marcelo Corrêa, 5.193 Fernando Rebelo, 5.194 Public domain, 5.196 Hermann Luyken, BASF, 5.196 Hermann Luyken, BASF, 5.198 Dr. Claudia Weidenthaler, Max-Planck-Institut für Kohlenfor­ schung, Mülheim an der Ruhr, 5.199 Museo de América, Madrid, 5.200 Biblio- thèque nationale de France, Paris, 5.201 Public domain, 5.202 Public domain, 5.202 Rizzoli Editore, Milano, 5.203 Public domain, Thomas Poppenwimmer, Universität Zürich, 5.204 Joachim Müllerchen -my grabdma, 5.204 Magnus 796 Directory of Illustrations

Manske, 5.206 SB_Johnny, 5.206 Tozeuma, 5.207 Gunther von Hagens, Institut für Plastination, Heidelberg, www.koerperwelten.de, 5.207 Gunther von Hagens, Institut für Plastination, Heidelberg, www.koerperwelten.de, 5.208 H.R.Ullrich, Deutsches Weinbaumuseum, Oppenheim, 5.210 Cheryl Backhouse, Australian National Botanic Gardens and Australian National Herbarium, Canberra, 5.210 H. Zell, 5.212 LiquidGhoul, 5.213 Bernd Schaefer, 5.214 Dr. Michael G. Weller, Bundesanstalt für Materialforschung und -prüfung, Berlin.

6. Hormones 6.1 Public domain, 6.3 Reinhard Kraasch, 6.4 Public domain, 6.4 Harimiao, 6.7 Terry Goss, 6.8 Public domain, 6.9 Boghog2 Public domain, 6.11 Forum concoursvaches.fr, 6.12 Jackie Esposito, PennState Archiv, 6.13 Rillke, 6.14 Ar- chiv, Bayer HealthCare, 6.15 Archiv, Bayer HealthCare, 6.16 Jock MacDonald Film, Inc., San Francisco, 6.17 Archiv, Bayer HealthCare, 6.18 Archiv, Bayer­ HealthCare, 6.19 Public domain, 6.20 Public domain, 6.21 Prof. Dr. Frithjof C. Kuepper, University of Aberdeen, Scotland, 6.22 Public domain, 6.24 Public domain, 6.25 Drahreg01, 6.26 Prof. Dr. Dietrich Grube, Medizinische Hoch- schule Hannover, 6.28 Dr. Ansgar Schäfer, BASF, 6.29 BASF, 6.30 Rizzoli Edi- tore, Milan, 6.31 Prof. S. Aoki, Gunma University, Maebashi, Japan, 6.32 Public domain, 6.34 Frank Vincentz, 6.40 Psychonaught, Public domain, 6.41 Public domain, 6.43 Laurie Devine, McGill University, Montreal, 6.44 Public domain.

7. Vitamins 7.1 www.serges.de, 7.2 Public domain, 7.2 Public domain, 7.3 Public domain, 7.4 Public domain, 7.5 Public domain, 7.6 Helena MacLean, Nova Scotia, Ca­ nada, 7.7 BASF, 7.7 BASF, 7.7 BASF, 7.9 Maulaff, 7.10 Hartley, William W., public domain, 7.10 Karl Meyer, Hoffmann-La Roche, 7.11 BASF, 7.12 BASF, 7.14 Martina Verdong-Dreher, Deutsche Akademie der Naturforscher Leopol- dina, Halle, 7.15 BASF, 7.16 Dr. Muhammad Zeeshan, Norwegian University of Science and Technology, Trondheim, Norway, 7.18 Markus Hagenlocher at de.wikipedia, 7.19 Public domain, 7.19 Polivka University of South Bohemia, Nove Hrady, Czech Republic, 7.20 Dr. Jens Rieger, BASF, 7.20 DSM, 7.21 Gut Gimritz (Germany), 7.22 Dr. Richard Sliwka,University Trondheim, 7.23 Papa­ kuro, 7.24 Bart Braun, 7.24 Hartmut Inerle, Imjustmatthew, 7.25 AXT dimer in β-crustacyanin. PDB crystal structure with code 1GKA, 7.26 Universitätsarchiv Heidelberg, Pos III 00112, Foto: Böhm, 7.29 BASF, 7.30 BC Salmon Farmers Association, 7.31 Judit Gamondele, Académie nationale de Pharmacie, Paris, 7.32 M. Hugentobler, DSM, 7.33 Rigues, 7.34 Frank Fox, Fachhochschule Trier, 7.34 Remi Jouan, 7.35 Harry Haikalis, BASF Australia, 7.35 Harry Haika- lis, BASF Australia, 7.36 International Rice Research Institute (IRRI), 7.36 pub- lic domain by its author, Petaholmes, 7.37 Public domain, 7.38 Historische Museen­ Hamburg, 7.39 BASF, 7.40 public domain, 7.41 Dr. Hyun_Soo Ko, Universitätsklinikum Heidelberg, 7.45 Smithsonian Institution, 7.45 BASF, 7.46 Jynto (talk), 7.47 Roman Kaiser, Givaudan, Vernier, Swiss, 7.48 Dr. Lionel Loew, Historisches Archiv Roche. Directory of Illustrations 797

8. Agrochemicals 8.1 D-click, 8.2 “Eine Geschichte des Pflanzenschutzes - Die Pflanzen schützen, den Menchen nützen, IVA”, 8.3 BASF, 8.4 Mueseum Unterlinden, Colmar, 8.5 BASF, 8.6 Public domain, 8.10 Mnolf, 8.11 Monsanto, 8.12 BASF, 8.12 Oudemansiella_mucida.jpg: Luisangel from León, Spain, derivative work: Ak ccm (talk), 8.13 BASF, 8.14 BASF, 8.14 Louisa Howard, 8.14 Klaus Hoff- meier, public domain, 8.16 Dr. Antje Wolf, BASF, 8.20 BASF, 8.20 BASF, 8.23 Dr. Benno Boes, Siegen, 8.29 Prof. Gongyin Y. E, Institute of Insect ­ Sciences, Zhejiang University, Hangzhou China, 8.29 Quartl, 8.33 Public domain,­ 8.34 Thomas Schüßler, Königsfeld, Public domain, 8.36 Stan Shebs, 8.36 Philippe Guillaume, 8.37 Dr. Nigel Unwin, MRC Laboratory of Molecular Biology, Cambridge, 8.38 Jon M. Lindstrom, University of Pennsylvania, 8.39 Thomas Brown, 8.40 Richard Ling, David Paul (photographer) and Dr. Bruce Livett (University of Melbourne), 8.41 John Heuser, Washington University School of Medicine, Saint Louis, Missouri, U.S.A, 8.45 Natasha Wright, Florida Department of Agriculture, 8.45 Consumer Services, Bugwood.org, 8.50 David Monniaux, 8.52 Clemson University – USDA Cooperative Extension Slide Series,­ Bugwood.org, 8.52 Whitney Cranshaw, Colorado State University, www. insectimages.org, 8.53 Esmat M. Hegazi, University of Alexandria, Bugwood. org, 8.53 Mike Stangeland & Kim Davis, 8.58 Susanne Uebele, Archiv der ­Max-Planck-Gesellschaft, Berlin-Dahlem, 8.59 P.gibellini, 8.70 Thomas Eisner, Cornell University, 8.72 Dr. Joachim Rheinheimer, 8.74 BASF, 8.75 BASF, 8.76 BASF, 8.78 BASF, 8.79 BASF, 8.80 Dr. Richard L. Wilson, Willapa Bay, Washington, 8.81 Raul Narciso C. Guedes, Dr. Nelsa Guedes, Departamento de Entomologia, Universidade Federal de Viçosa, Viçosa, Brasil, 8.82 Dr. Joachim Rheinheimer, 8.82 Dr. Joachim Rheinheimer, 8.83 public domain, 8.84 Dr. Joachim Rheinheimer, 8.85 Dr. Joachim Rheinheimer, 8.86 Alvesgaspar. Subject Index

A Acorus calamus 296 adventitia 405 Acremonium chrysoge- Aedes aegypti 679 Abbas, Haly 522 num 236, 247 Aegypiinae 324 Abbott 189, 274, 335, Actinia equina L. 607 African beer yeast 118 653 Actiniaria 607 African electric catfish Abelmoschus moschatus actinioerythrol 607 728 122 actinol 627, 632 African civet 120 (+)-cis-abienol 146 Actinomycetales 725 African peach 295 Abies balsamea 146 ACV-synthase 240 Africanus, Johannes Leo Abraham, Sir Edward acylase 246 141 Penley 236 (D)-acylases 185 Agamemnon 32 absolue 54, 77 acyloin condensation Agaricus bisporus 112 absorption maximum 368, 369 Agha, Mustafa 383 604 acyltransferase 246 Agkistrodon halys ACE 214 Adalat 209 ­blomhoffii 214 ACE Inhibitors 214 adalimumab 335 agonists 730 ACE-lisinopril complex Adams, Roger 300 agouti-related peptide 225 Adams, Stewart 323, 363 acetaminophen 320 334 agriculture 763 acetamiprid 737, 747 adenohypophysis 520, agrochemicals 2, 677 acetanilide 321 524, 525 Ahlquist, Raymond Perry acetoacetyl-CoA 407, adenosine 471 571 599 adenosine diphosphate Ajinomoto 193, 684 acetone 626 691 akashin 35 acetovanillone 112 adenosine triphosphate Akita, Hiroyuki 701 acetylcholine 569, 727, 471, 691 (D)-alanine 189, 192 731, 734 adenosine-5’-phosphate (L)-alanine 682 acetylcholine receptor 475 alanine 177, 185, 186, 732 adenosine-A1-receptors 486, 682 acetylcholinesterase 471 Alberts, Alfred W. 419 724 S-adenosylmethionine Alcaligenes eutrophus acetyl-CoA 598 65, 117, 422, 476, 486, 255 acetyl-CoA-carboxylase 569, 658, 690 alcohol dehydrogenase 660 adenylylcyclase 471 458 acetyllactic acid 369 adiposity 362 Alcon 340 15-O-acetyl-PGA2-­ adipoyl-7-aminodesace- aldehyde dehydro­genase 1 methylester 341 toxycephalosporanic 458 N-acetylphenylalanine acid 245, 246 Alder, Kurt 424 194 Adisseo 66, 610 aldolase 598 (R)-acetylphenylmetha- adrenal gland 565, 567 aldosterone 215, 520, nol 581 adrenal medulla 567, 528 acetylsalicylic acid 318 569 Aldrich, Thomas Bell achiote 637, 638 adrenal 529 567, 687 Aconitum napellus 566 adrenaline 265, 565–570 Algae 757

B. Schaefer, Natural Products in the Chemical Industry, DOI 10.1007/978-3-642-54461-3, © Springer-Verlag Berlin Heidelberg 2014 800 Subject Index

Alicyclobacillus acido- amino acid herbicides anabasine 490, 731 caldarius 155, 157 681 Anabasis aphylla 490 Alicyclobacillus amino acids 169 anaesthesia 268 ­acidoterrestris 598 (D)-amino acids 189 anaesthetics 268 Aliskiren 227 (2L)-amino-4-(methyl­ Anakinra 335 Alitame 190 phosphino)-butyric analgesic core structure alizarin 13, 14, 36 acid 682 267 alkaloids 727 2-amino-4-oxo-6-methyl­ analgesics 268 Allen & Hanburys 575, pteridine 475 Ananchenko, Sofya 578 (D)-aminoacid oxidase ­Nikolaevna 549 Allen, Albert D. 174 247 anandamide 304, 305, Allen-Doisy test 536 2-aminoanthraquinone 363 allethrolone 722, 723 20 Anarsia lineatella 766 Allevi, Pietro 41 γ-aminobutyric acid 725 anastrozole 535 Allopora californica 609 aminocarboxylase 661 anatoxin A 731 alloporin 609 7-aminocephalosporanic (+)-anatoxin A 491, 493, (1S)-B-allyldiisopino- acid 229, 246, 247 495 camphenylborane (6S)-7-aminodesacetoxy- Anchel, Marjorie 688 496 cephalosporanic acid Andersag, Hans 453 almonds 110, 721 244 Andersson, David A. 99 Alnitak 171 7-aminodesacetoxy­ androgenetic alopecia Alpine poppy 270 cephalosporanic acid 534 Altschul, Rudolf 415 229, 246 androstan-3β-ol-17-one alum 37, 40 aminodimethyluracil 478 541 Alzheimer, Alois 211 N-aminomethylphos­ androstadienedione 541 Amadori products 203 phonylacetic acid 686 5-androstene-3β,17β-diol Amadori rearrangement 6-aminopenicillanic acid 534 23, 202 9, 229, 235, 240, 244, androstene-3,17-dione Amadori, Mario 203 245 534, 535 Amanita muscaria 569, aminophenazone 322 androsta-4,16-dien-3-one 688, 727 3-aminopyridine 483 4, 139 Amauris ochlea 79 aminotransferases 192 5α-androst-16-en-3-ol 48 ambergris 140, 141 ammonia 682, 686 5-androsten-3β-ol-17-one Amberlyn® 143 ammonia reactor 175 534, 539, 541 ambrein 142 ammonolysis 224 5-androsten-3β-ol-17-one ambrettolide 121, 122 Amoore, John 49 acetate 539, 540, 545, α-ambrinol 142 amorpha-4,11-diene 552 (–)-ambrox 140, 142, 458, 463, 465 5α-androst-16-en-3-one 143, 145, 146, 153 amorpha-4,11-diene 4, 48 (+)-ambrox 143 synthase 458 Andrussow process 473 3a-epi-(–)-ambrox 143 amorphadiene-12-­ Andrussow, Leonid 9b-epi-Ambrox 143, 145 hydroxylase 458 473 ambroxan® 143 amoxicillin 190, 229, anethole 110 American cockroach 245, 248 angiogenesis 386 740 AMP 471 angiotensin converting American electric eel 728 (S)-amphetamine 576 215 American tobacco ampicillin 229, 245, 248 angiotensin I 215 ­hornworm 487 Amycolata autotrophica angiotensin-converting American wintergreen 653 enzyme 214 316 amygdalin 721 angiotensinogen 215 Amersham 653 Amylin Pharmaceuticals Anichkov, Nikolay Amgen 335 365 ­Nikolaevich 407 amidases 185 Amyris 464, 466 aniline 20 amidocarbonylation Anabaena circinalis 493 animal 47 193, 684 Anabaena flos-aquae 493 animal feed 180 Subject Index 801

Anke, Timm 689, 694 Arbusov reaction 618, (L)-aspartic acid 177, annelid 725 620 186, 249, 485 Anner, George 541 Archangelica officinalis Aspergillus nidulans 240 Anopheles 445, 679 Hoffm. 122 Aspergillus niger 658, Anopheles funestus 444 Archemycota 688 714 Anopheles gambiae 444 archil 14 Aspergillus ochraceus anopheline 444, 451 ARCO 770 714 anorectic 363 Arctiidae 758 Aspergillus oryzae 688 anorectic neurotrans­ Arens, Josef Ferdinand Aspergillus terreus 419, mitter 363 598 422, 428 antagonists 730 Aristotle 181, 534 Aspirin® 209, 315, 316, Antarctic krill 629 Arkema 127 317, 319 antennae 762 Arndt, Fritz 541 Assassin bugs 679 anthocyanidins 270 Arndt-Eistert reaction astacene 629 Anthonomus grandis 541 astaxanthin 5, 594, 603, 777 Arnstein peptide 240, 609, 611, 626, 627, 628, Antifebrin® 321 243 631, 636 antioncogene 386 534, 535 Asteraceae 688, 704 Antipyrine® 322 arteannuin B 459 Astra 575 aorta 404 artemether 466 AstraZeneca 8, 259, 335, Aphanizomenonflos- Artemisia absinthium L. 420, 433 aquae 493 79 AT1 receptor antagonist Aphidoidea 756 Artemisia annua 457 226 aphids 737, 756 artemisinic acid 459, 465 atabrine 453, 454 Aphis craccivora 737, 738 artemisinic alcohol 458, atenolol 577, 581 Apiaceae 688 465 atherosclerosis 403, 407, Apis mellifera 740, 755 artemisinic aldehyde 412 apo- 620 458, 459, 465 Atkinson 98 8’-apo-β-carotenal 611, artemisinic aldehyde- Atlantic electric ray 729 621, 624 Δ11(13)-reductase 458 Atlas moth 762 12’-apo-β-carotenal 621 (+)-artemisinin 438, Atochem 614 8’-apocarotenal 594 455, 456, 458, 461, 462, Atomaria linearis 749 apocarotenoids 620, 624 463, 464, 465, 466 atom efficiency 7 Apocynaceae 414 arteriosclerosis 403 213, 420, apolipoproteins 411 artesunate 466 430 apoptosis 386 Arthrobacter nicotinovo- ATP 471 Appel reaction 552 rans 488, 489 Attacus atlas 762 Appel, Rolf 552 arthropods 751 Aubry, Jean-Marie 463 Apple codling moth 766 [1,2]-aryl migration 332 Augustine 522 Aqua mirabilis 50 Arzneimittelwerke aureothin 690 Arabian coffee 468 ­Dresden 316 autocatalysis 172 Arabidopsis thaliana 82 asbestos 384 autocrine 339, 519 arachidonic acid 318, Aschoff, Karl Albert autonomic nervous 319, 336, 337, 338 Ludwig 406 ­system 569 arachidonoyl-2-glycerol Ascomycota 688 autopsy 404 305 Asiatic rice stem borer autumn crocus 388 arachidonoyldopamine 749 Avenzoar 383 305 Asinger reaction 192 Averroës 383 arachidonoylethanol- Asinger, Friedrich 192 Avery, Mitchell 461 amide 305 Asivatham 88 Avicenna 261, 468, 522 N-arachidonoylserine Asparagus officinalis avidin 657 305 180 Axel, Richard 45 Arachis hypogaea 336 aspartame 181, 193 Axelrod, Julius 321 Arachnida 757 aspartases 186 axoneme 387 Aratani, Tadatoshi 711 (D)-aspartic acid 192 azetidinone 250 802 Subject Index

azlactone 233 Barton, Sir Derek 146, Bernal, John Desmond azoospermia 553 545, 648 406 Azotobacter vinelandii Barton-Hesse Calcitriol Bestmann-Ohira reagent 172 synthesis 648 778 azoxystrobin 696, 704 Basedow, Carl von 555 beta blockers 571, 576, Aztecs 108 BASF 9, 15, 19, 26, 28, 577 Azzaro pour Homme® 30, 40, 41, 66, 67, 69, betamipron 252 159 106, 130, 143, 174, 473, Betula lenta 316 541, 610, 612, 614, 616, Beyer, Peter 640 617, 619, 620, 622, 625, 416 B 631, 639, 641, 662, 695, Bialaphos 683 696, 697, 698, 763 biapenem 259 baccatin III 400 Basidiomycota 688 Bichat, Marie-Francois- Bachmann, Werner Basta 681 Xavier 383 ­Emmanuel 541 Bastianelli, Giuseppe bicycloheptane 342 Bacillus proteolyticus 444 Bignami, Amico 444 193 bathochromic shift 605 bilharziasis 446 Bacillus sphaericus 186, Baumann, Eugen 21, 555 Bill & Melinda Gates 660 Baumé, Antoine 276 Foundation 464 Bacillus subtilis 682 Baur, Albert 50, 123 BINAP 102, 104, 138 Bacterium pyocyaneus Baxter, James G. 598 Bingen, Hildegard of 231 Bayer 15, 210, 211, 277, 50, 297, 313 Bactrocera oleae 780 420, 453, 551, 698 biochemistry 6 Baeyer, Adolf von 15, 20, Bayer Agrochem 745 biocide ban 685 26, 122, 451 Bayer CropScience 734 Biocon 428 Baeyer-Drewsen ­reaction Bayer Cross 317 biocytin 657 26 Bayer, Ernst 681 biotin 593, 654, 655, 659 Baeyer-Villiger ­oxidation Bayer/Schering 340 biotin content 655 85, 89, 129, 135, 254, bc1-complex 691 biotinidase 657 256, 342, 344, 356, 714, beadlet anemone 607 biotin-synthase 659 772 Becker 277 ε-N-biotinyllysine 657 baker’s yeast 527, 580, Beckett 98 Birch reduction 312, 642, 654 Beckmann rearrangement 543, 544, 547, 549, 550 Bakhle, Yeshwant S. 217 539 Birch, Arthur John 542, Balaenoptera musculus Beecham Pharma­ceuticals 543 140 418 birth control pills 526 Baldwin rules 149, 242 Beet leafminers 749 bis-(2-chloroethyl)- Baldwin, Sir Jack Edward beetles 725, 753 sulfide 385 241 Behrendt, H.-J. 100 bis(chloromethyl)ether balsam fir 146 Belgian cheeses 607 384 Bamford-Stevens reaction Beller, Matthias 766 α-bisabolol 598 461 bene-Arzneimittel 321 Bischler-Möhlau indole Banded cucumber beetle Bentley, Kenneth 284 synthesis 432 738 benzaldehyde 110, 191 Bischler-Napieralski Bang, Oluf 385 benzazepine 494 reaction 288 Baran, Phil 7 benzene 214, 384 Bixa orellana 637 Barbas III, Carlos 550 benzil-benzilic acid cis-bixin 637, 638 Barbasco 537, 539 ­rearrangement 368 Black-bellied clerid 751 Barbier process 275 benzo[a]pyrene 384 black grapes 319, 320 Barclay, Arthur 390 benzoic acid 315 black salsify 108 Barker, George 571 (L)-benzylsuccinic acid Black sea rod 340 Bark-gnawing beetle 751 217 Black Widow 217 Barthel, William F. 707 Beraldo, Wilson T. 216 Black, Sir James 577 Barton reaction 545, Bergmann, Per 214 Blakeslea trispora 637 779 beriberi 591 Blanc, Gustave 54 Subject Index 803

blastocyst 525 Bouffard 254 buprenorphine 286 Blattella germanica 737 Bouveault, Louis 54 Burgess reagent 427 Blattodea 756 Bowers, Albert 545 Burgundy-blood algae Blindeyes 270 BPP5a 217 493 Bloch, Konrad Emil 406, Brabander, Jef De 780 Burns, Allan 554 530 brachycera 756 Butenandt, Adolf 535, Blondeau, Philippe 100 Braconnot, Henri 180 537, 751, 763 blood schizont 445 bradykinin 216, 265 Buthus occitanus 217 blood-vessel 405 Brassica napus 529 butorphanol 289 blue jeans 19, 29 brassinolide 528 button mushrooms Blue poppy 270 von Braun reaction 286 112 Blue whales 140 brazilin 13, 14 Byers, Larry D. 217 blue-green algae 493 Breckpot-Grignard Blue-Jeans-Look 30 β-lactam cyclisation BlueStar 610 255 C BMS 15, 401, 420 Bredereck, Hellmut 478 boar 48 Bredt, Konrad Julius 598 C14-aldehyde 622, 623 Body-Mass-Index 362 Bredt’s Rule 543 C16-aldehyde 623 Boehringer Ingelheim Brevibacterium flavum C19-aldehyde 623 8, 15, 226, 491, 575, 186, 187, 660 C6-aldehyde 624 578, 579 Brevibacterium linens C17,20- 534 Boehringer Mannheim 605, 607 cabazitaxel 402 416 brevicomin 773, 774 cabbage moth 758 Bohn, René 15, 19 Bristol-Myers 417 Cabreúva 150 Boiga irregularis 322 Bristol-Myers-Squibb Caesar, Julius 18 bolas spiders 751 217, 390 caffeine 467, 471, 476, Boletus edulis 688 Brockmann, Hans 642 478, 479 Bolinea lutea 690 Brodie, Bernard 321 Cahn-Ingold-Prelog boll weevil 777 broiler 595 priority rules 780 boll weevil song 679 2-brom-4’-nitroacetophe- Calabar beans 527 bombykol 751 none 579 Calamus 296 Bombyx mori 529, 751 Brook rearrangement Calandra oryzae 749 Bonaparte, Napoleon 50 254 calcinosis 644 Bondt, Jacob de 591 Brooke, Blyth 236 calcitriol 643, 648, 653 bone softening 642 Brotzu, Giuseppe 236 calcium-regulating sterols Bonrath, Werner 666 Brown algae 555, 556 529 Boord, Cecil E. 717 brown planthopper 735 Californian electric ray Boord reaction 717 brown tree snake 322 728 Boots Company 323, Brown, Geoffrey D. 458 Cambridge Antibody 328, 592 Brown, Michael S. 412 Technology 335 Boots-Hoechst-Celanese Brown, Wade H. 446 Camellia sinensis 469 328 de Bruyn, Cornelis cAMP 471 Boreostereum vibrans ­Adriaan Lobry van Campari, Gaspare 41 366 Troostenburg 203 camphor tree 566 boric acid 523 Buchanan, John M. 473 Canada balsam 146 Borregaard 112, 763 Büchi, George 58, 148 cancer 382 Bortels, Hermann 172 Buchner, Johann Andreas candesartan cilexetil Bosch, Carl 174 315 226 Botanica-Mex S.A. 539 Buck, Linda B. 45 Candida albicans 701 Bothrops jararaca 214, Buddrus, Joachim 632 Candida boidinii 186 216 bugs 756 Candida rugosa 220 Botryodiplodia malorum bulbus olfactorius 46 Candida tropicalis 134 552 α-bungarotoxin 730–732 Candida utilis 220 Botrytis cinerea 681 Bungarus multicinctus Candolle, Augustin-­ Böttiger, Paul 15 730, 732 Pyrame de 678 804 Subject Index

Canis lupus familiaris Caribbean sea whip 340 cephalosporin C 229, 751 Carl Zeiss Company 443 237, 239, 241, 247 Cannabaceae 298 carmine 14, 37 cephalosporium cannabichromene 300, carminic acid 13, 39, ­acremonium 236 303 40, 41 cepham antibiotics 236 cannabichromenic acid Caro, Heinrich 22, 40, Cepionate® 92 303 452 Cerioli, Gaspare 482 cannabichromenic acid (1R)-cis-caronaldehyde 420 synthase 303 hemiacetal 718 cervical cancer 386 cannabicyclol 303 α-carotene 603, 604 Cetalox 143, 147, 148 (–)-cannabidiol 310 β-carotene 56, 57, 65, Cetonia aurata 17 cannabidiol 298, 300, 303 594, 597, 603, 611, 617, Ceylon tea 79 cannabidiolic acid 303 622, 623, 636 Chagas’ disease 679 cannabidiolic acid β-carotene process 619 Chain, Ernst Boris 231 ­synthase 303 Carotenoids 593 Chan, Albert S. C. 347 cannabielsoic acid A 303 carotenoproteins 609 Chanel No. 19® 77 cannabigerol 303 Carothers, Wallace Hume Chanel No. 5® 51, 118, cannabigerolic acid 303, 133 139, 159 304 Carpinus betulus 85 Chanel, Coco 51 cannabinerol 303 Carroll reaction 66, 150 Chang, Min-Chueh 546 cannabinerolic acid 303 carrots 593, 597 chanterelles 593 cannabinoid receptor Carson, Rachel 451, 679 Charlemagne 37, 50, 297 type 1 304 Carus, Titus Lucretius 49 Charpentier, Paul 731 cannabinoid receptor, (+)-carvone 146, 701 Chatin, Gaspard Adolphe type 2 304 Casas, Bartholomé de 555 cannabinol 298, 301, 303 las 481 Chatt, Joseph 174 cannabinolic acid 303 Casida, John E. 747 Chaudret ruthenium cannabis 296 cassava 721 hydrogenation catalyst Cannabis sativa L. 296, cassette-transporter 159 298, 566 comatose 82 chelotropic extrusion 651 Canon of Medicine 261, Cassis procedure 53 chemical communication 440 Castillo, Bernal Díaz del 750 canthaxanthin 594, 603, 480 chemoreceptors 727 611, 625, 627, 636 Casutt, Michael 661, 670 Chevreul, Michel Eugène n-caproic acid 302 catechol 567 406 capsaicin 98, 110 catecholamine-O-methyl- chickens 591 capsanthin 594 571 chilli peppers 110 Capsicum annuum 110 catecholamines 265 Chilo suppressalis 725, captopril 209, 218, 219, Catha edulis 566, 573 749 220 (–)-(S)-cathinone 573 Chiraphos 107, 196 caput quadratum 641 Cativa process 556 Chirotech Technology carbacycline 358 Caucasian insect-flower Ltd. 353 carbapenem ­antibiotics 704 chloramphenicol 228, 249 Caucasian insect powder 580, 666 Carbide and Carbon 704 chlordiazepoxide 664 Chemical Corporation Caventou, Joseph chlormadinone acetate 711 ­Bienaimé 142, 315, 448 547 Carbone, Tito 446 cefadroxil 229, 245 2-chloro-5-(chloro­ carbonyl-ene reaction Cela Merck/Shell 763 methyl)pyridine 741 103 celecoxib 326, 327, 334 2-chloro-5-(chloro­ carboxylases 660 cell division 386 methyl)thiazole 743 carboxypeptidase A 217 Centocor Inc. 335 N,N-bis-(2-chloroethyl) Cárdenas, Luis Ernesto cephalexin 229, 245, methylamine 385 Miramontes 211 248 2-chloro-5-methylpyridine (+)-2-carene 311 cephalosporin 228, 236 741 Subject Index 805

6-chloronicotinic acid 741 cinchonidine 331 cochineal 38 chloroplast 83 cinchonine 723 cochineal red A 38, 40 chloroquine 453, 454 cinchonism 453 Cochrane, Charles Stuart chlorpromazine 730, 731 cinnamaldehyde 110 492 chocolate 108, 305 cinnamic acid 116, 315 cockroaches 756 cholecalciferol 528, 643, Cinnamomum camphora cocoa 108, 305, 469 644, 645 566 cocoa beans 470 cholecalciferol-25- cinnamon 110 (–)-codeine 270, 271, hydroxy­lase 643 circularly polarised light 273, 275, 277, 282, 283 cholecystokinin 363 172 codeinone 273 5α-cholesta-7,24-dien- Cistus labdaniferus 143 Codeinone reductase 3β-ol 532 citral 9, 68, 69, 612 273 406, 408, 411, citranaxanthin 611, 621 Codexis 431 418, 436, 527, 530, 532 citric acid cycle 176 coenzyme A 418 cholesterol acetate 645 (+)-(R)-citronellal 106, Coffea arabica 468 cholic acid 416 107, 463 Coffea canephora 468 choline 731 (S)-citronellal 768 Coffee blossom 469 cholinergic synapse 724 citronellal 68, 103, 768 Coffee cherries 469 chondrites 170 (–)-(S)-citronellol 106 Coffee leaf miner moth Chondrodendron (+)-(R)-citronellol 106 767 ­tomentosum 492, 730 citronellol 54, 68 Cognis 143, 639 chorionic gonadotropin Citrus sinensis 590 Cohn, Edwin Josef 409 525 civet 120 cola 469 chorismic acid 22, 23, civetone 121, 132, 139 Cola nitida 469 117, 179, 315 Civettictis civetta 120 colchicine 388 Chortoglyphus arcuatus CK one® 92 Colchicum autumnale 123 Claisen condensation 388 chrysanthemic acid 132, 700 Cole, William 33 2, 10, 711, 718 Claisen reaction 367, coleoptera 725, 753 cis-chrysanthemic acid 368, 369, 683 417 715 Claisen rearrangement β-collidine 449 (1R)-trans-chrysanthemic 66, 67, 89, 93, 148, 425, colophony 101 acid 715 612, 713, 715, 718, 722 Colorado beetles 749 Chrysanthemum cinera­ clary sage 143, 144 Colorado potato beetle riifolium 704, 705 clary sage oil 145 451 Chrysanthemum Claviceps purpurea 527, colourants 5, 13 ­coccineum 704 678 Colton, Frank B. 544 Chrysanthemums 705 Clemmensen reduction Columbus, Christopher (+)-chrysanthenol 309 126, 133 297, 480 (–)-chrysanthenone 309 clenbuterol 575, 579, 580 Columella, Moderatus Chugai 335 Clercq, Pierre J. De 661 441 chylomicron 411 416 Commerçon, Alain 395, Ciba 15, 414, 541 Clonorchis sinensis 385 398 Ciba-Geigy 227, 254, Clostridium isatidis 30 Common housefly 740 255, 329, 698, 737, 747 Clostridium pasteuria- Common Soapwort 537 cicadas 737, 749 num 172 Common wheat bunt Cilag 686 clothianidin 748 678 cilastatin 252 cloves 110 competitive antagonists cilia olfactoria 46 Club des Hashischins 297 730 cimetidine 577 Cnaphalocrocis medinalis conception 525 Cimicifuga europaea 492 725, 749 condoms 522 cinchona bark 315 Cobo, Barnabé de 447 cone snail 730, 732 Cinchona ledgeriana 448 cobratoxin 728 congo red 16 Cinchona officinalis 447 cocaine-amphetamine- Conidae 730 Cinchona tree 447 related transcript 363 coniferin 111, 115 806 Subject Index

coniferyl alcohol 111, 115 cowpea aphid 738 [3 + 2]-cycloaddition α-conotoxins 732 COX-1 318, 325 668 Conradi, Benjamin COX-2 318, 325 cycloartenol 531 ­Gottlob Friedrich 527 COX-2 inhibitors 327 cyclocitral 58 Conrad-Limpach reaction COX-Inhibitors 325 cyclododecatriene 127, 453 crabs 594 131 conrotatory 646 Crabtree catalyst 137 1,3-cycloelimination contact process 28, 41 craniotabes 641 712–714 contraception 521, 522 Craven, Lawrence 317 cycloheptadecanone 122 Conus imperialis 732 m-cresol 100, 101, 777 cycloiridal 66 Conus magnus 732 cretinism 554 336, 337 Conus textile 732 Crick, Francis 210 cyclooxygenase-1 318 Convallaria majalis 69, crocetin dialdehyde cyclooxygenase-2 319 106 631 cyclopentadecanone 122 Convallariae herba 542 crocin 13, 608 cyclopentenolones 722 Cook, Silas 463 Crocus sativus L. 14 o-cyclopentylphenol 582 Coolact P® 99 cross-linked enzyme cyclopropanation 101 Coolant Agent 10® 99 ­aggregates 248 (D)-cycloserine 190 copper sulfate 678 cross-linked enzyme Cyclosia Base® 69 Corey epoxidation 130 crystals 248 Cylindorsperum 493 Corey lactone 342, 343, α-crustacyanin 609 cyphellopsis 690 353 β-crustacyanin 609, 610 cysteamine 746 Corey, Elias J. 200, 342, Cryptococcus albidus cysteine 178, 659 530, 550, 713, 770 146 cystine 182 Corey-Bakshi-Shibata Cryptococcus cytidine triphosphate reduction 345 ­neoformans 134 600 Corey-cyclopropanation crystal 576 cytisine 492, 494, 495, 552 cucurbit powdery mildew 731 Corey-Fuchs reaction 693 cytisism 493 719 Culex-mosquito 439 Cytisus laburnum 492 Coriandre® 95 Culpeper, Nicholas 314 Cytisus scoparius 492 corn mint 95 Cuon alpinus 324 cytochrome 692 corn poppy 270 Cupressus sempervirens cytochrome bc1 693 γ-coronal 142 143 cytochrome-bc1-complex coronatine 81 curare 727 692 corpus albicans 526 curcuma 14 cytochrome B5 reductase Corpus Hippocraticum Curcuma longa L. 14, 458 261, 313, 383, 404, 440 319, 320 cytochrome P450 708 corpus luteum 525 curcumin 13, 320 cytochrome P450 corpus luteum graviditatis­ curettage 120 ­reductase 458 525 Curie, Iréne 385 Cortés, Hernán 108 Curvularia lunata 714 cortexone 533 Cushman, David 217 D corticosterone 528, 533, cyanidin 270 536 cyanobacteria 493 Dactylopius coccus Costa corticotropin 520 cyanohydrins 720, 721 38 cortisol 528, 533, 536 α-cyclase 603 Dactylopius coccus L. 14 520, 533, 536 β-cyclase 603 DAISO 770 Corynebacterium gluta­ ε-cyclase 603 Dakin-West reaction 658 micum 187, 188, 657 cyclic 3’,5’-adenosine Dale, Sir Henry Hallett Cotesia marginiventris monophosphate 471 571, 727 81 [2 + 1]-cycloaddition Dalmatian insect-flower cotinine 490 252, 711, 715, 716 704 Cotton boll weevil 679 [2 + 2]-cycloaddition Dalmatian insect powder Courtois, Bernard 556 371, 778 704 Subject Index 807

Dalmatian iris 64 deltamethrin 710 dichlorisoprenaline 577 Dalton 172 Demole, Edouard 78 3,4-dichloro-1,2,5-­ Daly, John W. 492 Dendroctonus brevicomis thiadiazol 582 β-damascenone 56, 57 751, 773 dichloro-diphenyl-tri- damascone 52, 55 Dendroctonus frontalis chloroethane 451 α-damascone 58, 59, 61 Zimmermann 772 5,5’-dichloroindigo 35 β-damascone 56, 57, 58 Dendroctonus diclofenac 324, 330 Damask rose 52 ­ponderosae 772 Dieckmann cyclisation Danaidae 758 deoxyadenosine 658 84, 87, 91, 122, 541, 661 Danaus plexippus 758 3-deoxy-(D)-arabino- Diels, Otto Paul Hermann Dane-anhydride 248 heptulonic acid- 424 Daniphos 105 7-phosphate 179 Diels-Alder adduct 648 Danishefsky diene 426 deoxyquinine 450 Diels-Alder reaction 41, Danishefsky, Samuel 392 1-deoxyxylulose-5-­ 89, 285, 286, 293, 311, DAPA-synthase 658 phosphate 600 344, 422, 426, 463, 498 dart-poison frog 492 deoxyxylulose phosphate Diels-Alderase 423, 424 Darwin, Charles 521 pathway 302 dienogest 547, 548 Darzens reaction 147, dependence 265, 269 Diesbach, Henri de 15 328, 622 depolymerisation 133 N,N-diethylgeranylamine Daucus carota 597 Derosne, Charles 276 102 Davidoff Cool Water® desacetoxycaphalosporin N,N-diethylnerylamine 159 C 243 102 Davies, Stephen 376 desacetoxycephalosporin Digitalis purpurea 537 Daviet, Laurent 145 241 dihomo-γ-linolenoyl­ Davis, Jacob 19 10-desacetyl-2-debenzoyl­ ethanolamide 305 DDT 451, 679 baccatin III 399 dihydroartemisinic acid deaminases 192 10-desacetylbaccatin III 458, 463, 465 decaffeination 477 390, 393, 399 dihydroartemisinic decarboxylases 661 10-desacetylbaccatin III- ­aldehyde 458 degradation 682 10 O-acetyltransferase dihydroartemisinin Degussa 9, 28, 183, 186, 399 466 188, 192 Descartes, René 264 dihydrocodeine 283 Degussa methionine desmosterol 532 γ-dihydroionone 142 process 183 desogestrel 549 dihydro-β-ionone 148 dehydratase 423 desoxyxylulose-5-­ dihydrojasmone 86 (+)-dehydroabietylamine phosphate-reducto­ (–)-dihydromorphine 664 600 283 dehydroambra oxide 142 Dess-Martin oxidation 3,4-dihydro-4,3-retro- 5,5a-dehydroambrox 157 550 φφ-carotene-3,3-dione 24-dehydrocholesterol destraction 477 606 527 dethiobiotin 658, 659 5α-dihydrotestosterone 7,8-dehydrocholesterol dethiobiotin-synthase 534 532, 642, 645 659 1,2-dihydroxyanthra­ 5α,6α-dehydrogenase 531 Diabetes mellitus 205 quinone 39 dehydrolinalool 69, 612 Diabrotica balteata 737, dihydroxyindolinecar- 16-dehydropregnenolone 738 boxylic acid 570 539 Diagoras of Melos 261 3,3’-dihydroxyisoreniera- 16-dehydropregnenolone diallyl adipate 91 tene 594, 605, 606 acetate 538 7,8-diaminopelargonic 2,3-dihydroxyisovaleric 3-dehydroquinic acid 117 acid 658 acid 369 1,2-dehydroreticulinium diamorphine 277 2,6-dihydroxy-N-­ reductase 273 diazepam 664 methylmyosmine Delft cleavage 245 diazo transfer 250, 717 489 Delia antiqua 749 5,5’-dibromoindigo 34 (L)-3,4-dihydroxyphenyl- delphinidin 270 6,6’-dibromoindigo 34 alanine 195, 570 808 Subject Index

2,6-dihydroxypseudo- docosahexaenoic acid Dunaliella salina 639 oxynicotine 489 320 DuPhos 197 2,5-dihydroxypyridine docosa-7,10,13,16-tetra­ DuPont 15, 133, 225, 489 enoylethanolamide 637, 734 2,6-dihydroxypyridine 305 Dürer, Albrecht 442, 641 489 Dodds, Edward Charles Dutch Resolution 187 diketopiperazines 721 540 Duus, Fritz 768 diketopyrrolopyrrole 16 N-dodecanoylsarcosine Dwarf Breadseed Poppy dimethylallyl diphosphate 194 270 407, 599, 600 Dog rose 53 dyer’s knotweed 18 N,N’-dimethylbarbituric dogbane 414 dyer’s whin 492 acid 478 Dohme 419 dynorphin 267 2,7-dimethylocta-2,4,6- Domagk, Gerhard 210 dysphoria 266 trienedial 618 domino reaction 149 DyStar 30 dimethylurea 478 domino-Michael/aldol N,N’-dimethylurea 477 reaction 347 1,3-dimethyluric acid 478 (L)-DOPA 101, 186, E dimethylvioluric acid 478 195, 199 Dimroth, Otto 39 dopachrome 570 E 605® 710 dinoprost 340 DOPA-decarboxylase earthy 47 dinoprostone 340 570 Eau de Chypre 52, 95 dinotefuran 739, 740, 748 dopamine 265, 273, 568, Eau de Cologne 50 (+)-DIOP 103 570 Eau Sauvage® 79 dioscin 537 dopamine-β-hydroxylase Eaux fraîches 79 570 ebelactone B 366 537, 539 dopaquinone 570 Ebers Papyrus 439, 522 Dioscorea floribunda 537 doripenem 259 Ebert 87 Dioscorea macrostachya Dorp, David Adriaan α-ecdysone 528 537 van 598 Echerichia coli 188 Dioscorea mexicana 537, Dow AgroSciences 725 echinenone 594 538 Dow Chemical Corpora- ecstasy 576 Dioscorea tokoro 537 tion 711 Eden® 95 2, 527, 537, Dowpharma 431 Eder, Ulrich 550 538, 539 doxycycline 455 Edman 682 Dioskurides, Pedanius DPP-IV 365 Edwin Smith Papyrus 261, 389, 522 Dragoco 15, 54 439 diosone 538 Dreser, Heinrich 317 egg yolks 595 dioxin 558 (–)-drimenol 146 Eggers Doering, William dioxindole 20 drospirenone 551 von 448 dioxygenase 604 Dr. Rudolf Maag AG 698 egg-white 657 (R,R)-DIPAMP 195 drug market 212 Eglantine rose 53 dipeptidylpeptidase-4 Drummond, Sir Jack Egyptian cotton worm 364, 365 Cecil 591, 592 738 dipivefrine 575 Dryden Jr., Hugh L. 541 Ehrenstein, Maximilian direct sympathomimetic DSM 9, 66, 185, 187, 542 575 191, 193, 245, 610, 637, Ehrlich-Ascites discovery 7 644, 653, 666, 671, 721 ­carcinoma cells 690 Dishman 653 Duboisia hopwoodii Ehrlich-Ascites tumour disiamylborane 152 490, 491 cells 689 disparlure 769, 771 Duchesne, Ernest 231 Ehrlich, Paul 210, 405, disrotatory 646 Dufour, Philippe Sylvestre 452, 727 Djerassi, Carl 211, 540, 470 Eichengrün, Arthur 317 544, 546 Duisberg, Carl 317, 321 eicosanoids 336, 339 dobutamine 575, 578 Dumas, Jean Baptiste 5,8,11,14-eicosatetraenoic docetaxel 395 315 acid 336 Subject Index 809

Eijkman, Christiaan 591 Enos, William F. 409 ethyl 3-methyl-2-thioxo- Eisai 523 enoylreductase 423 imidazole-1-carboxylate Eisleb, Otto 290 enterobactin 315 561 Eistert, Bernd 541 enzymatic kinetic ethyl-DuPHOS 93 van Ekenstein, Willem ­resolution 710, 720 ethylenediamine 744 Alberda 203 enzymatic resolution ethylvanillin 110 electroantennogram 762 224 ethynodiol diacetate 546 electroantennographic enzyme-membrane- ethynylation 543, 544 detector 762 reactor 185 ethynyloestradiol 543, electrocarboxylation 332 Ephedra sinica 566 549 electrocyclic ring-closure (1R,2S)-ephedrine 566, 17α-ethynyl-steroids reactions 646 576, 581 543 Electron transport chain ephedrine 580, 663 etilefrine 575 691 (–)-epibatidine 491, 492, etoricoxib 327 Electrophorus electricus 495, 497, 498, 731 etorphine 284 728, 740 epimerisation 244 Eugenia caryophyllata electroplaques 729 epinephrine 565 110 elegance 8 Epipedobates tricolor eugenol 110, 116 elegance 7 492 Eugster, Conrad 598 elegant syntheses 9 epoprostenol 357 eukaryotes 228 elephant 751 epothilone 402 Euler-Chelpin, Ulf Svante Elephas maximus 751 epoxysqualene 66 von 336, 567 Eli Lilly 15, 244, 312, Epstein-Barr virus 385 Euphausia superba 629 361, 365, 578, 725 Erdmann, Otto Linné 20 Euphausiacea 594 elicitors 81 ergocalciferol 642, 648 euphoria 265 Ellermann, Vilhelm 385 (3α, 5β, 24R)-ergostan-3-ol Eupoecilia ambiguella elymus 685 142 765 Emmerich, Rudolf 230 ergosterol 527, 642 European grapevine moth Ems-Chemie 127 ergot 678 765 emtricitabine 213 ergot fungus 527 European larch 157 enalapril 221 ergotism 678 European salmon 595 enalaprilate 221, 222 eribulin 402 European spruce bark enantioselective Erlenmeyer-Plöchl beetle 751, 775 ­autoinduction 722 ­reaction 195 European yew 389, 393, enantioselective ertapenem 259 566 ­protona­tion 59 Erysiphaceae 678 Eurygaster integriceps Endo, Akira 417, 419 Erysiphe graminis tritici 108 endocannabinoids 304, 697 Evans, David 311 305, 321 erythrose 117 Evonik 127, 183 endocrine 519 (D)-erythrose-4-­ exaltolide 121, 122, 126, endocrine glands 519 phosphate 117, 179 133 endocrine system 520 Eschenmoser fragmenta- exaltone 121, 122, 126, 7-endo-dig 780 tion 128 127 endometrium 525 Eschenmoser, Albert 149 exciton coupling 609 β-endorphine 267, 363 Escherichia coli 30, 186, exemestane 535 6-endo-trig cyclisations 247, 598, 658 exenatide 364, 365 149 esomeprazole 213 exocytosis 732 enfleurage 53, 63, 77 esterastin 366 exophthalmos 555 Engel pharmacy 276 estragole 110 6-exo-dig 780 English Disease 641 d’Estrées, Gabrielle 4 5-exo-trig reaction 149 English holly 493 ethisterone 543 expandase 246 English violet 63 ethyl 2-hydroxy-2-methyl­ extraction 637 enisoprost 348, 349, 353 but-3-enoate 621 417 enkephalin 267 ethyl 8’-apo-β-carotenoate Enoclerus lecontei 751 611, 621, 625 810 Subject Index

F Firmenich 45, 51, 58, 61, formiate dehydrogenase 90, 93, 105, 137, 143, 186 FAD 304 144, 145, 152, 153, 157 Formicidae 753 FADH2 304 Fischer esterification 345 N-formylkynurenine 485 Fahlberg, Constantin 333 Fischer, Emil 49, 470, 477 N10-formyltetrahydro­ Farkaš, J. 715 Fischer, Otto 15 folic acid 475 Fallopius, Gabriel 522 fish oil 319, 644 Fourcroy, Comte de 470 Farina, Giovanni Maria Fishermen’s Friend 107 fractional distillation 101 50 flamingo 593 fragrances 4, 45 (E,E)-farnesol 151, 152 flash pyrolysis 540 Francis, George 493 farnesyl diphosphate flash vacuum pyrolysis Francke, Wittko 767 408, 436, 458, 465, 529, 129 Frangipani 50 601 Flattum, Roger F. 740 Franz, John E. 687 faropenem 259 flavin adenine dinucleo- Frederick the Great 314 fatty acids 757 tide 302 Frederickson, Donald S. Favorskii rearrangement Flavobacterium lutescens 410 701, 715 188 Freudenberg, Karl 112 feedback mechanism flavours 45 Freund 277 520 Fleming, Sir Alexander Friedel-Crafts acylation Fehr, Charles 61, 125, 158 3, 210, 231, 688 41, 224, 328, 330, 332, FEMA 4496 99 flies 756 334, 579 FEMA 4549 99 Florey, Howard W. 231 Friedel-Crafts alkylation female sexual functions flosulide 327 123, 126, 312 525 Flower, Roderick J. 322 Friedländer, Paul 34 Feminis, Giovanni Paolo flufenamic acid 324 Friedrich Bayer & Co. de 50 fluorophenylalanine 321 416 185 Fritsche Dodge and fentanyl 292 fluprostenol 353 Olcott 146 Fenton reaction 459 flurbiprofen 324 Fritzsche, Carl Julius 18 Feringa, Ben L. 347 fluticasone 213 Frølich, Theodor 590 fermentation 192, 466, fluvalinate 190 frontalin 772, 773 698 420, 421, 432 frontier orbital 646 Fermi, Enrico 557 fly agaric 569, 688, 727 C. E. Frosst & Co. 581 Ferreira, Sérgio Henrique FMC 717, 718 Frost 116 216, 217 Fodéré, François-­ fructose 598 ferriprotoporphyrin IX Emmanuel 554 fruit body 688 446, 450 foliage 593 fruity 47 ferriprotoporphyrin IX- folic acid 593 FSH 524, 525 quinine complex 450 Folkers, Karl August fuchsine 16, 384 ferrous protoporphyrin 407, 654 fucosterol 527 IX 446 follicles 525 Fucus vesiculosus 555 fertilised egg 524 follicle-stimulating fumaric acid 186 ferulic acid 115, 116 ­hormone 48, 524 fungi 228, 688 Fetid bugbane 492 follitropin 524 Funk, Kazimierz 591 Feuer, Henry 734 Food and Drug Admin- Fürstner, Alois 135 416 istration 261, 311, Fusarium moniliforme fibrous cap 413 419, 546 391 Field poppy 270 foot odour 607 Field rose 53 forestry 763 Fieser, Louis F. 606 Forge, Frederick B. La G filia olfactoria 46 707, 722 Filipendula ulmaria 313, formaldehyde 472 galaxolide 123, 124 314 formamide 473 Galen of Pergamon 404 finasteride 534 formamidine insecticides Galenus, Claudius 49, fipronil 724 472 383, 404, 729 Subject Index 811

Gallus gallus domesticus glandula suprarenalis Golden rice 640 591 565 Goldscheider, Alfred 98 gametocytes 445 Glandula thyreoidea 554 Goldstein, Joseph L. 412 Garden angelica 122 Glandula uropygialis 123 Golgi, Camillo 444 Garden angelica root Glauber, Johann Rudolf golimumab 335 122 678 gonadotropin-releasing gardenia 79 Glaxo 437, 610 hormone 524 gardenia flowers 79 Glaxo synthesis 562 gonadotropins 520, 524 Garnham, Cyril 444 GlaxoSmithKline 8, 231, Good Manufacturing Gaskell, Walter Holbrook 274, 415, 575 Practice 8 569 global challenges 1 Goodyear, Charles 523 gastric juice 349 glomeruli 46 Gorgonia coral 340 Gates, Marshall D. 279 Glomset, John 410 Gorham, Paul 493 Gaubius, Hieronymus h-GLP-1 364, 365 gout 729 David 98 glucagon-like-peptide-1 Graebe, Carl 38 Gaultheria procumbens 363, 365 Graham 322 316 glucocorticoids 318 Gram, Christian 230 Gause, Georgyi glucoferulic acid 116 gramicidin S 190 ­Frantsevitch 190 glucose 598 grandisol 778, 779 Gautschi, Markus 100 glufosinate 683, 684 grandlure 777 geese 123 glutamate 180, 686 Granit, Ragnar Arthur Geigy 15, 210, 451, 679 glutamate dehydrogenase 596