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List of Abbreviations 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 liver 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, Pfizer, 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.
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