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Abbreviations Abbreviations 9-BBN 9-Borabicyclo[3.3.1]nonane Ac Acetyl Ad Adamantyl AD Asymmetric dihydroxylation AIBN Azo-bis-iso-butyronitrile ATPase Adenosine triphosphatase BHT Butylhydroxytoluene BIA Bioinductive assay Bn Benzyl Boc t-Butyloxycarbonyl BOP-Cl Bis(2-oxo-3-oxazolidinyl)phosphonic chloride brsm Based on recovered starting material Bu Butyl BuLi n-Butyllithium Bz Benzoyl CAN Cerium ammonium nitrate CBS Corey-Bakshi-Shibata catalyst Cbz Benzyloxycarbonyl CNS Central nervous system CoA Coenzyme A cod 1,5-Cyclooctadiene CSA Camphorsulfonic acid Cys Cysteine dba Dibenzylideneacetone DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DCC Dicyclohexyl carbodiimide DDQ 2,3-Dichloro-5,6-dicyanobenzoquinone DEAD Diethyl azodicarboxylate DET Diethyl tartrate DHP Dihydropyran S. Bra¨se et al., The Chemistry of Mycotoxins, Progress in the Chemistry of Organic 233 Natural Products, Vol. 97, DOI 10.1007/978-3-7091-1312-7, # Springer-Verlag Wien 2013 234 Abbreviations DHQ Dihydroquinidine DIAD Diisopropyl azodicarboxylate DIBAL Diisobutyl aluminum DIPEA Diisopropyl ethyl amine DIPT N,N-Diisopropyltryptamine DKP Diketopiperazine DMAP Dimethylaminopyridine DMDO Dimethyldioxirane DME Dimethoxyethane DMF Dimethylformamide DMP Dess-Martin periodinane DMSO Dimethylsulfoxide DNA Desoxyribonucleic acid DPPA Diphenylphosphoryl azide dppbenz 1,2-Bis(diphenylphosphino)benzene dppp 1,3-Bis(diphenylphosphino)propane dr Diastereomeric ratio DTBMP di-t-Butylmethylpyridine EDC (N-Ethyl-N0-(3-dimethylaminopropyl)carbodiimide ee Enantiomeric excess EEDQ 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline EGF Epidermal growth factor ELEM Equine leukoencephalomalacia equiv. Equivalents er Enantiomeric ratio Et Ethyl EU European Union Fmoc Fluorenylmethyloxycarbonyl h Hour HATU N,N,N0,N0-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate HBTU O-Benzotriazole-N,N,N0,N0-tetramethyl-uronium hexafluorophosphate HIV Human immunodeficiency virus HMDS Hexamethyldisilazane HMPA Hexamethylphosphoramide HOAt Hydroxy-7-azabenzotriazole HOBt N-Hydroxybenzotriazole HPLC High-performance liquid chromatography Hsp Heat shock protein IBX 2-Iodoxybenzoic acid IC Inhibitory concentration IPC Isopinocampheyl kDa kilodalton Abbreviations 235 KHMDS Potassium bis(trimethylsilyl)amide LAH Lithium aluminum hydride LD Lethal dose LDA Lithium diisopropylamide Leu Leucine LiDBB Lithium 4,40-di-tert-butyl biphenyl LiHMDS Lithium bis(trimethylsilyl)amide m-CPBA meta-Chloroperbenzoic acid Me Methyl MIDA N-Methyliminodiacetic acid MOM Methoxymethyl Ms Mesyl MS Molecular sieves MTBE Methyl tert-butyl ether MW Microwave NaHMDS Sodium bis(trimethylsilyl)amide NBS N-Bromosuccinimide NCS N-Chlorosuccinimide Nep1 Necrosis and ethylene-inducing peptide1 NHK Nozaki-Hiyama-Kishi NIS N-Iodosuccinimide NLP Nep1-like protein NMM N-Methylmorpholine NMO N-Methylmorpholine oxide NMR Nuclear magnetic resonance Ns 2-Nitrophenylsulfonyl OMST O-Methylsterigmatocystin PCC Pyridinium chlorochromate PDC Pyridinium dichromate Ph Phenyl PHAL Phthalazine Phe Phenylalanine Phth Phthaloyl Piv Pivalyl (= 2,2-dimethylpropanoyl) PLE Porcine liver esterase PMB Paramethoxybenzyl ether PPTS Pyridinium para-toluenesulfonate PPY 4-(1-Pyrrolidinyl)pyridine Pr Propyl Pro Proline PS Polystyrene PTSA para-Toluenesulfonic acid Py Pyridine R Residue 236 Abbreviations RAL Resorcylic acid lactones Red-Al Sodium bis(2-methoxyethoxy)aluminum hydride RNA Ribonucleic acid ROS Reactive oxygen species rt Room temperature SEM [2-(Trimethylsilyl)ethoxy]methyl Sia Siamyl (1,2-dimethylpropyl) SPhos 2-Dicyclohexylphosphino-20,60-dimethoxybiphenyl t tert- TBAF tetra-butyl ammonium fluoride TBAI tetra-butyl ammonium iodide TBDPS tert-butyldiphenylsilyl TBHP tert-butyl hydroperoxide TBS tert-butyldimethylsilyl TBU 1,8-Diazabicyclo[5.4.0]undec-7-ene TCA Tricarboxylic acid TDKP Thiodiketopiperazine TEA Triethylamine TEMPO (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl Tf Triflyl TFA Trifluoroacetic acid TFAA Trifluoroacetic acid anhydride THF Tetrahydrofuran THP Tetrahydropyranyl TIPS Triiso-propyl silyl TLC Thin-layer chromatography TMEDA N,N,N0,N0-Tetramethylethylenediamine TMP 2,2,6,6-Tetramethylpiperidine TMS Trimethylsilyl TMSE Trimethylselenonium Tol Toluyl TPAP tetra-propylammonium perruthenate TPPTS 3,30,300-Phosphinidynetris(benzenesulfonic acid) trisodium salt Tr Trityl (=triphenylmethyl) Ts para-Toluenesulfonyl Val Valine WSC 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride References 1. Richard JL (2007) Some Major Mycotoxins and their Mycotoxicoses—an Overview. Int J Food Microbiol 119:3 2. Hussein HS, Brasel JM (2001) Toxicity, Metabolism, and Impact of Mycotoxins on Humans and Animals. Toxicology 167: 101 3. http://publications.tamu.edu/publications/Corn/B-1279%20Mycotoxins.pdf 4. Turner NW, Subrahmanyam S, Piletsky SA (2009) Analytical Methods for Determination of Mycotoxins: a Review. Anal Chim Acta 632: 168 5. Robbins CA, Swenson LJ, Nealley ML, Gots RE, Kelman BJ (2000) Health Effects of Mycotoxins in Indoor Air: a Critical Review. Appl Occup Environ Hyg 15: 773 6. Winssinger N, Barluenga S (2007) Chemistry and Biology of Resorcylic Acid Lactones. Chem Commun: 22 7. Martins, MB, Carvalho, I (2007) Diketopiperazines: Biological Activity and Synthesis. Tetrahedron 63: 9923, and references cited therein 8. Fox, EM, Howlett, BJ (2008) Biosynthetic Gene Clusters for Epipolythiodioxopiperazines in Filamentous Fungi. 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Wong JJ, Hsieh DPH (1976) Mutagenicity of Aflatoxins Related to Their Metabolism and Carcinogenic Potential. Proc Natl Acad Sci USA 73: 2241 18. Carnaghan RBA, Hartley RD, O’Kelly J (1963) Toxicity and Fluorescence Properties of the Aflatoxins. Nature 200: 1101 19. Schuda PF (1979) Aflatoxin Chemistry and Syntheses. Top Curr Chem 91:75 20. Asao T, Bu¨chi G, Abdel-Kader MM, Chang SB, Wick EL, Wogan GN (1963) Aflatoxins B and G. J Am Chem Soc 85: 1706 21. Asao T, Bu¨chi G, Abdel-Kader MM, Chang SB, Wick EL, Wogan GN (1965) The Structures of Aflatoxins B and G1. J Am Chem Soc 87: 882 S. Bra¨se et al., The Chemistry of Mycotoxins, Progress in the Chemistry of Organic 237 Natural Products, Vol. 97, DOI 10.1007/978-3-7091-1312-7, # Springer-Verlag Wien 2013 238 References 22. Brechbu¨hler S, Bu¨chi G, Milne G (1967) The Absolute Configuration of the Aflatoxins. J Org Chem 32: 2641 23. Stubblefield RD, Shotwell OL, Shannon GM, Weisleder D, Rohwedder WK (1970) Parasiticol: A New Metabolite from Aspergillus parasiticus. J Agric Food Chem 18: 391 24. Ashoor SH, Chu FS (1975) Reduction of Aflatoxins B1 and B2 with Sodium Borohydride. J Assoc Off Anal Chem 58: 492 25. Dutton MF, Ehrlich K, Bennett JW (1985) Biosynthetic Relationship among Aflatoxins B1, B2, M1, and M2. Appl Environ Microbiol 49: 1392 26. Do JH, Choi D-K (2007) Aflatoxins: Detection, Toxicity, and Biosynthesis. Biotechnol Bioprocess Eng 12: 585 27. Butler WH, Clifford JI (1965) Extraction of Aflatoxin from Rat Liver. Nature 206: 1045 28. Reiss J (1968) Mykotoxine. Z Allg Mikrobiol 8: 303 29. Hsia MTS (1982) Toxicological Significance of Dihydrodiol Metabolites. J Toxicol – Clin Toxicol 19: 737 30. Wogan GN, Edwards GS, Newberne PM (1971) Structure-Activity Relationships in Toxicity and Carcinogenicity of Aflatoxins and Analogs. Cancer Res 31: 1936 31. Wogan GN (1966) Chemical Nature and Biological Effects of the Aflatoxins. Bacteriol Rev 30: 460 32. Verma RJ (2004) Aflatoxin Cause DNA Damage. Int J Hum Genet 4: 231 33. Reiss J (1971) Inhibition of Fungal Sporulation by Aflatoxin. Arch Mikrobiol 76: 219 34. Bu¨chi G, Foulkes DM, Kurono M, Mitchell GF (1966) The Total Synthesis of Racemic Aflatoxin B1. J Am Chem Soc 88: 4534 35. Bu¨chi G, Foulkes DM, Kurono M, Mitchell GF, Schneider RS (1967) The Total Synthesis of Racemic Aflatoxin B1. J Am Chem Soc 89: 6745 36. Bu¨chi G, Weinreb SM (1969) The Total Synthesis of Racemic Aflatoxin-M1 (Milk Toxin). J Am Chem Soc 91: 5408 37. Bu¨chi G, Weinreb SM (1970) Total Syntheses of Aflatoxins M1 and G1 and an Improved Synthesis of Aflatoxin B1. J Am Chem Soc 93: 746 38. Roberts JC, Sheppard AH, Knight JA, Roffey P (1968) Studies in Mycological Chemistry. Part XXII. Total Synthesis of (±)-Aflatoxin-B2. J Chem Soc: 22 39. 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