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The Chemistry of Mycotoxins

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1. Auflage 2013. Buch. xv, 300 S. Hardcover ISBN 978 3 7091 1311 0

Format (B x L): 15,5 x 23,5 cm Gewicht: 665 g

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1 Introduction . . . 1

2 Aflatoxins . . . 3

2.1 Biological Properties . . . 7

2.2 Total Syntheses of Aflatoxins . . . 8

2.2.1 Total Syntheses of Racemic Aflatoxins . . . 8

2.2.2 Enantioselective Total Syntheses of Aflatoxins . . . 11

2.3 Syntheses of Aflatoxin Building Blocks . . . 13

2.3.1 Syntheses of Building Blocks for Aflatoxins B2and G2 . . . 13

2.3.2 Syntheses of Building Blocks for Aflatoxins B1and G1 . . . 15

2.3.3 Synthesis of a Building Block for Aflatoxin M2 . . . 16

2.3.4 Enantioselective Syntheses of Aflatoxin Building Blocks . . . 17

2.4 Syntheses of Biosynthetic Aflatoxin Precursors . . . 18

3 Citrinin . . . 23

3.1 General . . . 23

3.2 Total Syntheses of Citrinin . . . 24

4 Ergot Alkaloids . . . 27

4.1 Structural Subclasses of Ergot Alkaloids . . . 28

4.1.1 Tricyclic Precursors of Ergot Alkaloids . . . 28

4.1.2 Clavine-Type Alkaloids . . . 29

4.1.3 Ergoamides . . . 31

4.1.4 Ergopeptines . . . 31

4.1.5 Related Structures . . . 33

4.2 Biological Properties . . . 34

4.3 Total Syntheses . . . 35

v

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4.3.7 Biomimetic Three-Step Synthesis of Clavicipitic Acids . . . 46

5 Fumonisins . . . 49

5.1 Biological Properties . . . 51

5.2 Total Syntheses . . . 51

5.2.1 Total Synthesis of Fumonisin B1 . . . 51

5.2.2 Enantioselective Total Synthesis of Fumonisin B2 . . . 54

5.2.3 Total Synthesis of AAL-toxin TA1 . . . 57

6 Ochratoxins . . . 61

6.1 Biological Properties . . . 62

6.2 Total Syntheses . . . 63

6.2.1 Enantioselective Total Synthesis of (R)-Ochratoxin aand Ochratoxins A, B, and C . . . 63

6.2.2 Total Syntheses of Racemic Ochratoxinsaand Ochratoxins A, B, and C . . . 64

6.2.3 Total Syntheses of All Stereoisomers of Ochratoxin A . . . 66

7 Patulin . . . 69

7.1 General . . . 69

7.2 Total Syntheses of Patulin . . . 70

8 Trichothecenes . . . 73

8.1 Biological Properties . . . 76

8.2 Total Syntheses . . . 76

8.2.1 Non-Macrocyclic Trichothecenes . . . 76

8.2.2 Macrocyclic Trichothecenes . . . 83

9 Resorcylic Acid Lactones . . . 91

9.1 Biological Properties . . . 92

9.2 Total Syntheses . . . 93

9.2.1 Total Syntheses of Zearalenone . . . 94

9.2.2 Total Synthesis of Zearalenol . . . 98

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9.2.3 Total Synthesis of Radicicol . . . 100

9.2.4 Total Synthesis of Hypothemycin . . . 102

9.2.5 Total Synthesis of Aigialomycin D . . . 104

9.2.6 Total Synthesis of Pochonin C . . . 107

10 (Thio)diketopiperazines . . . 109

10.1 Biological Properties . . . 111

10.2 Total Syntheses . . . 112

10.2.1 DKP Total Syntheses . . . 112

10.2.2 TDKP Total Syntheses . . . 118

11 AlternariaMetabolites . . . 127

11.1 Biological Properties . . . 129

11.2 Total Syntheses . . . 131

11.2.1 Total Synthesis of Alternariol and Alternariol 9-Methyl Ether . . . 131

11.2.2 Total Synthesis of Altenuene and Isoaltenuene . . . 133

11.2.3 Total Synthesis of Dehydroaltenusin . . . 134

11.2.4 Total Synthesis of Neoaltenuene . . . 136

11.2.5 Total Synthesis of Tenuazonic Acid . . . 137

12 Skyrins . . . 139

12.1 Biological Properties . . . 143

12.2 Syntheses of Skyrin Model Systems . . . 145

12.3 Total Syntheses of Skyrins . . . 149

13 Xanthones . . . 153

13.1 Xanthones . . . 155

13.1.1 Bikaverin . . . 155

13.1.2 Pinselin and Pinselic Acid . . . 155

13.1.3 Sterigmatocystin and Derivatives . . . 156

13.1.4 Nidulalin A . . . 164

13.2 Tetrahydroxanthones . . . 166

13.2.1 Blennolides . . . 166

13.2.2 Dihydroglobosuxanthone . . . 172

13.2.3 Diversonol . . . 173

13.2.4 Diversonolic Esters . . . 179

13.3 Hexahydroxanthones . . . 180

13.3.1 Applanatins . . . 180

13.3.2 Isocochlioquinones . . . 181

13.3.3 Monodictysins . . . 182

13.4 Xanthone Dimers and Heterodimers . . . 183

13.4.1 Acremoxanthones . . . 183

13.4.2 Vinaxanthones . . . 184

13.4.3 Xanthofulvin . . . 187

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13.5.12 Sch 54445 . . . 204

13.5.13 Xanthonol . . . 205

14 Cytochalasans . . . 207

14.1 Biological Properties . . . 210

14.2 Total Syntheses . . . 213

14.2.1 Total Synthesis of Cytochalasin B and L-696,474 . . . 213

14.2.2 Total Synthesis of Proxiphomin . . . 216

14.2.3 Total Synthesis of Cytochalasin H . . . 217

14.2.4 Total Synthesis of Cytochalasin G . . . 218

14.2.5 Total Synthesis of Cytochalasins D and O . . . 219

14.2.6 Total Synthesis of ( )-Aspochalasin B . . . 220

14.2.7 Total Synthesis of Zygosporin E . . . 222

15 Peptidic Mycotoxins . . . 225

15.1 Biological Properties . . . 226

15.2 Total Syntheses . . . 228

15.2.1 Total Synthesis of Pithomycolide . . . 228

15.2.2 Total Synthesis of Ustiloxins D and F . . . 228

15.2.3 Total Synthesis of Malformin C . . . 229

15.2.4 Total Synthesis of Unguisin A . . . 231

Abbreviations . . . 233

References . . . 237

Author Index . . . 273

Subject Index . . . 295

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