Total synthesis of natural products: at the frontiers of organic chemistry
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| Other Authors: | |
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| Format: | Book |
| Language: | English |
| Published: |
Berlin [u.a.]
Springer
2012
|
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XVI, 279 S. Ill., graph. Darst. 235 mm x 155 mm |
| ISBN: | 3642340644 9783642340642 |
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CONTENTS
1 NOMININE 1
KEVIN M. PEESE AND DAVID Y. GIN
1.1 INTRODUCTION AND CLASSIFICATION 1
1.2 PHARMACOLOGY 2
1.3 BIOSYNTHESIS 3
1.4 PREVIOUS SYNTHETIC WORK 3
1.4.1 TOTAL SYNTHESIS OF NOMININE [19A] 4
1.4.2 SYNTHETIC STUDIES TOWARD THE HETISINE ALKALOIDS 6
1.5 STRATEGY AND RETROSYNTHESIS 7
1.6 SYNTHESIS 9
1.7 COMPLETE SYNTHESIS 20
REFERENCES 21
2 NAKITERPIOSIN 25
SHUANHU GAO AND CHUO CHEN
2.1 BACKGROUND 25
2.2 SYNTHESIS OF THE 6,6,5,6 STEROIDAL SKELETON 26
2.2.1 THE BIOMIMETIC APPROACHES 27
2.2.2 THE RING-BY-RING APPROACHES 28
2.2.3 MISCELLANEOUS 28
2.3 SYNTHESIS OF NAKITERPIOSIN 31
2.4 BIOLOGY OF NAKITERPIOSIN 34
REFERENCES 34
3 THE KINAMYCINS 39
SETH B. HERZON
3.1 INTRODUCTION 39
3.2 STRUCTURE ELUCIDATION 41
3.3 BIOLOGICAL ACTIVITY AND MECHANISM OF ACTION STUDIES 43
3.4 BIOSYNTHESES OF THE KINAMYCINS 45
IX
HTTP://D-NB.INFO/1025943694
X
CONTENTS
3.5 SYNTHESES OF THE KINAMYCINS 46
3.5.1 SYNTHESIS OF (*)-KINAMYCIN C [24] 46
3.5.2 SYNTHESIS OF ()-0-METHYL-KINAMYCIN C [32] 51
3.5.3 SYNTHESES OF (*)-KINAMYCINS C, F, AND J [39] 54
3.5.4 SYNTHESIS OF (*)-KINAMYCIN F [45] 59
REFERENCES 64
4 A SHORT SYNTHESIS OF STRYCHNINE FROM PYRIDINE 67
DAVID B. C. MARTIN AND CHRISTOPHER D. VANDERWAL
4.1 INTRODUCTION 67
4.2 SYNTHESIS OF STRYCHNINE: A HISTORICAL PERSPECTIVE 68
4.3 STRUCTURAL CHALLENGES 71
4.4 BACKGROUND: ZINCKE ALDEHYDES 73
4.5 BACKGROUND: INTRAMOLECULAR CYCLOADDITIONS OF INDOLES 75
4.6 DEVELOPMENT OF THE INTRAMOLECULAR DIELS-ALDER CYCLOADDITION
OF TRYPTAMINE-DERIVED ZINCKE ALDEHYDES 78
4.7 SYNTHESIS OF NORFLUOROCURARINE 80
4.8 PROTECTING GROUPS ARE NOT ALWAYS EVIL 84
4.9 STRATEGIES FOR D-RING FORMATION FOR STRYCHNINE 87
4.10 SOME UNUSUAL APPROACHES TO C15-C20 BOND FORMATION 92
4.11 A SUCCESSFUL ROUTE TO STRYCHNINE 93
4.12 CONCLUSIONS 98
REFERENCES 99
5 BRYOSTATIN 7 103
YU LU AND MICHAEL J. KRISCHE
5.1 INTRODUCTION 103
5.2 PHARMACOLOGY 104
5.3 BIOSYNTHESIS 106
5.4 PREVIOUS SYNTHETIC WORK 108
5.4.1 TOTAL SYNTHESIS OF BRYOSTATIN 7 (MASAMUNE 1990) 108
5.4.2 TOTAL SYNTHESIS OF BRYOSTATIN 2 (EVANS 1998) 110
5.4.3 TOTAL SYNTHESIS OF BRYOSTATIN 3 (NISHIYAMA
AND YAMAMURA 2000) 112
5.4.4 TOTAL SYNTHESIS OF BRYOSTATIN 16 (TROST 2008) 113
5.4.5 SYNTHESIS OF BRYOSTATIN 1 (KECK 2011) 115
5.4.6 SYNTHESIS OF BRYOSTATIN 9 (WENDER 2011) 117
5.5 STRATEGY AND RETROSYNTHESIS 118
5.6 SYNTHESIS 120
5.6.1 SYNTHESIS OF A-RING FRAGMENT 68 120
5.6.2 SYNTHESIS OF C-RING FRAGMENT 69 121
5.6.3 FRAGMENT UNION AND TOTAL SYNTHESIS OF BRYOSTATIN 1. . 123
5.7 CONCLUSION 127
REFERENCES 127
CONTENTS XI
6 SERRATEZOMINE A 131
JULIE A. PIGZA AND JEFFREY N. JOHNSTON
6.1 INTRODUCTION AND CLASSIFICATION 131
6.2 PHARMACOLOGY 132
6.3 BIOSYNTHESIS 133
6.4 PREVIOUS SYNTHETIC WORK 136
6.4.1 TOTAL SYNTHESIS OF SERRATININE 136
6.4.2 SYNTHETIC APPROACHES TOWARDS THE FRAMEWORK OF
SERRATININE 138
6.5 STRATEGY AND RETROSYNTHESIS 139
6.6 SYNTHESIS 141
6.7 COMPLETE SYNTHESIS 152
REFERENCES 152
7 HYPOCRELLIN/CERCOSPORIN 157
CAROL A. MULROONEY, ERIN M. O'BRIEN, AND MARISA C. KOZLOWSKI
7.1 INTRODUCTION 157
7.2 BIOLOGICAL ACTIVITY 159
7.3 PREVIOUS SYNTHETIC WORK 161
7.3.1 SYNTHESIS OF (*)-PHLEICHROME AND (*)-CALPHOSTIN
A,D [30] 161
7.3.2 SYNTHESIS OF (-)-CALPHOSTIN D [31] 162
7.3.3 SYNTHESIS OF (*)-PHLEICHROME AND (*)-CALPHOSTIN A
[32A] 163
7.3.4 SYNTHESIS OF (*)-CALPHOSTIN A-D [33A] 164
7.4 CONFORMATIONAL PROPERTIES 166
7.5 STRATEGY AND RETROSYNTHESIS 167
7.6 SYNTHESIS 170
7.6.1 SYNTHESIS OF (-)-HYPOCRELLIN A 170
7.6.2 SYNTHESIS OF (+)-PHLEICHROME AND (+)-CALPHOSTIN D 172
7.6.3 SYNTHESIS OF (+)-CERCOSPORIN 174
7.7 SYNTHESIS OF PERYLENEQUINONE ANALOGS 175
REFERENCES 179
8 PHOMACTIN A 183
YU TANG, KEVIN P. COLE, AND RICHARD P. HSUNG
8.1 INTRODUCTION 183
8.1.1 ISOLATION 183
8.1.2 BIOSYNTHESIS 185
8.1.3 MEDICINAL CHEMISTRY 185
8.1.4 SYNTHETIC CHALLENGES 185
8.2 THE ARCHITECTURALLY DISTINCTIVE ABD-TRICYCLE 186
8.2.1 RETROSYNTHETIC ANALYSIS 186
8.2.2 APPROACHES TO THE OXA-ANNULATION PRECURSOR 188
8.2.3 AN IMPROVED SYNTHESIS OF OXA-ANNULATION PRECURSOR . . . 190
XLL
CONTENTS
8.2.4 KEY OXA-ANNULATION AND THE D-RING ATROPISOMERISM . . . 191
8.2.5 A FORMAL SYNTHESIS OF (*)-PHOMACTIN A 194
8.3 LESSONS LEARNED FROM THE CHALLENGING STRUCTURAL TOPOLOGY . . . . 195
8.3.1 OXIDATIONS OF C3 AND C3A IN B-RING 195
8.3.2 REDUCTION OF C8A AND C8B AT THE AB-RING JUNCTION . 196
8.3.3 HOMOLOGATION AT C5A IN THE A-RING 197
8.4 COMPLETION OF THE TOTAL SYNTHESIS 202
8.4.1 THE DIENE ROUTE 202
8.4.2 THE ALLYL ALCOHOL ROUTE 203
8.4.3 THE VINYL EPOXIDE ROUTE 203
8.5 CONCLUSION 207
REFERENCES 207
9 (+)-LL,LL-DIDEOXYVERTICILLIN A 211
JUSTIN KIM AND MOHAMMAD MOVASSAGHI
9.1 INTRODUCTION AND CLASSIFICATION 211
9.2 PHARMACOLOGY 213
9.3 BIOSYNTHESIS 214
9.4 PREVIOUS SYNTHETIC WORK 216
9.4.1 PREVIOUS APPROACHES TO THE C3-C3'DIMERIC LINKAGES . . . 217
9.4.2 PREVIOUS APPROACHES TO THE EPIDITHIODIKETOPIPERAZINE
MOTIF 218
9.4.3 TOTAL SYNTHESIS OF EPIDITHIODIKETOPIPERAZINE ALKALOIDS . . 220
9.5 STRATEGY AND RETROSYNTHESIS FOR (+)-L 1,11'-DIDEOXYVERTICILLIN A .
222
9.5.1 SYNTHESIS OF (+)-L 1,1
L'-DIDEOXYVERTICILLIN A 223
9.5.2 GENERALIZATION TO THE EPIPOLYTHIODIKETOPIPERAZINE
ALKALOIDS 230
9.6 CONCLUSION 231
REFERENCES 231
10 RETIGERANIC ACID 235
DAVID R. ADAMS AND TOMAS HUDLICKY
10.1 INTRODUCTION 235
10.2 ISOLATION AND STRUCTURE 236
10.3 BIOSYNTHESIS 238
10.4 APPROACHES TO TOTAL SYNTHESIS 239
10.4.1 HUDLICKY 239
10.4.2 FALLIS 241
10.4.3 FRASER-REID 243
10.4.4 TRAUNER 244
10.5 TOTAL SYNTHESES 247
10.5.1 COREY 247
10.5.2 PAQUETTE 249
10.5.3 WENDER 252
10.5.4 HUDLICKY 255
10.6 CONCLUSIONS AND FUTURE PERSPECTIVES 256
REFERENCES 256
CONTENTS XIII
11 TOTAL SYNTHESIS OF THE LYCOPODIUM ALKALOID COMPLANADINE A . . . . 259
RICHMOND SARPONG AND DANIEL F. FISCHER
11.1 INTRODUCTION 259
11.2 BIOSYNTHESIS 259
11.3 BIOLOGICAL ACTIVITY 262
11.4 THE SIEGEL SYNTHESIS OF COMPLANADINE A 263
11.5 STRATEGY AND RETROSYNTHESIS 264
11.6 BORYLATIVE C-H FUNCTIONALIZATION 267
11.6.1 BENZENE RING FUNCTIONALIZATION: HARTWIG SYNTHESIS
OF TAIWANIAQUINOL B 267
11.6.2 PYRROLE RING FUNCTIONALIZATION: GAUNT SYNTHESIS
OF RHAZINICINE 268
11.6.3 INDOLE RING FUNCTIONALIZATION: MOVASSAGHI
SYNTHESIS OF THE ASPERAZINE CORE 269
11.7 COMPLETION OF THE COMPLANADINE A SYNTHESIS 269
11.8 APPLICATION OF THE STRATEGY TO LYCOPLADINES F AND G 270
11.9 CONCLUSION 271
REFERENCES 271
INDEX 273 |
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| title | Total synthesis of natural products at the frontiers of organic chemistry |
| title_auth | Total synthesis of natural products at the frontiers of organic chemistry |
| title_exact_search | Total synthesis of natural products at the frontiers of organic chemistry |
| title_full | Total synthesis of natural products at the frontiers of organic chemistry Jie Jack Li ... eds. |
| title_fullStr | Total synthesis of natural products at the frontiers of organic chemistry Jie Jack Li ... eds. |
| title_full_unstemmed | Total synthesis of natural products at the frontiers of organic chemistry Jie Jack Li ... eds. |
| title_short | Total synthesis of natural products |
| title_sort | total synthesis of natural products at the frontiers of organic chemistry |
| title_sub | at the frontiers of organic chemistry |
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