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
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
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
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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