Metathesis in natural product synthesis: strategies, substrates and catalysts
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| Other Authors: | |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2010
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XXVII, 384 S. Ill., graph. Darst. |
| ISBN: | 9783527324408 |
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Record in the Search Index
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VII CONTENTS FOREWORD V PREFACE XV LIST OF CATALYSTS XIX LIST OF
CONTRIBUTORS XXI ABBREVIATIONS XXV 1 SYNTHESIS OF NATURAL PRODUCTS
CONTAINING MEDIUM-SIZE CARBOCYCLES BY RING-CLOSING ALKENE METATHESIS 1
NICOLAS BLANCHARD AND JACQUES EUSTACHE 1.1 INTRODUCTION 1 1.2 FORMATION
OF FIVE-MEMBERED CARBOCYCLES BY RCM 1 1.3 FORMATION OF SIX-MEMBERED
CARBOCYCLES BY RCM 11 1.4 FORMATION OF SEVEN-MEMBERED CARBOCYCLES BY RCM
22 1.5 FORMATION OF EIGHT-MEMBERED CARBOCYCLES BY RCM 30 1.6 FORMATION
OF NINE-MEMBERED CARBOCYCLES BY RCM 33 1.7 FORMATION OF 10-MEMBERED
CARBOCYCLES BY RCM 34 1.8 CONCLUSION 39 REFERENCES 40 2 NATURAL PRODUCTS
CONTAINING MEDIUM-SIZED NITROGEN HETEROCYCLES SYNTHESIZED BY
RING-CLOSING ALKENE METATHESIS 45 SEBASTIAAN (BAS) A. M. W. VAN DEN
BROEK, SILVIE A. MEEUWISSEN, FLORIS L. VAN DELFI, AND FLORIS P. J. T.
RUTJES 2.1 INTRODUCTION 45 2.2 FIVE-MEMBERED NITROGEN HETEROCYCLES 47
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/996919309 DIGITALISIERT
DURCH VIII CONTENTS 2.2.3.2 2.2.4 2.3 2.3.1 2.3.1.1 2.3.1.2 2.3.1.3
2.3.1.4 2.3.2 2.3.3 2.4 2.5 2.6 3 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 3.8.1
3.8.2 3.8.3 3.9 POLYHYDROXYINDOLIZIDINES 55 PYRROLIZIDINE ALKALOIDS 59
SIX-MEMBERED NITROGEN HETEROCYCLES 61 PIPERIDINE ALKALOIDS 61
PIPERIDINES 61 PIPERIDINE CARBOXYLIC ACIDS 66 PIPERIDONES 68
POLYHYDROXYPIPERIDINES 69 INDOLIZIDINE ALKALOIDS 70 QUINOLIZIDINE
ALKALOIDS 73 SEVEN-MEMBERED NITROGEN HETEROCYCLES 78 EIGHT-MEMBERED
NITROGEN HETEROCYCLES 81 CONCLUSION 82 REFERENCES 83 SYNTHESIS OF
NATURAL PRODUCTS CONTAINING MEDIUM-SIZE OXYGEN HETEROCYCLES BY
RING-CLOSING ALKENE METATHESIS 87 JON D. RAINIER INTRODUCTION 87
CONTENTS IX ACKNOWLEDGMENT 144 REFERENCES 144 5 SYNTHESIS OF NATURAL
PRODUCTS CONTAINING MACROCYCLES BY ALKENE RING-CLOSING METATHESIS 149
ANA GRADILLAS AND JAVIER PEREZ-CASTELLS 5.1 INTRODUCTION 149 5.2
ORGANIZATION OF THE CHAPTER 151 5.3 MACROCYDIC POLYKETIDES 152 5.3.1
RESORCINYLIC MACROLIDES 152 5.3.2 SALICYLATE MACROLIDES 155 5.3.3 OTHER
ANTIBIOTIC MACROLIDES 158 5.3.4 MACROCYDIC MUSK 162 5.3.5 EPOTHILONES
163 5.3.6 AMPHIDINOLIDES 165 5.3.7 OTHER POLYKETIDES 167 5.3.8 NATURAL
CYDOPHANES 168 5.4 TERPENOIDS 169 5.4.1 DITERPENOIDS 169 5.4.2
MACROCYDIC LIPIDS 171 5.5 MACROCYCLES OF AMINO ACID ORIGIN 172 5.5.1
MACROLACTAMS 172 5.5.2 CYCLODEPSIPEPTIDES 173 5.5.3 ALKALOIDS 174 5.6
MACROCYDIC GLYCOLIPIDS 175 5.7 CONCLUSIONS AND OUTLOOK 177 REFERENCES
178 X CONTENTS 7.3.1 RCAM AS A SYNTHETIC STRATEGY 210 7.4 APPLICATIONS
OF RCAM IN NATURAL PRODUCT SYNTHESIS 211 7.4.1 RCAM/HYDROGENATION
STRATEGIES 211 7.4.1.1 MACROCYDIC MUSKS 211 7.4.1.2 PROSTAGLANDIN
LACTONES 212 7.4.1.3 SOPHOROLIPID LACTONE 213 7.4.1.4 EPOTHILONE A 213
7.4.1.5 CRUENTAREN A 215 7.4.1.6 LATRUNCULINS A, B, C, M, AND S 216
7.4.1.7 MYXOVIRESCIN AI 218 7.4.2 RCAM AND ALTERNATIVE ALKYNE
MANIPULATIONS 218 7.4.2.1 CITREOFURAN 218 7.4.2.2 AMPHIDINOLIDE V 221
7.5 CONCLUSIONS 221 REFERENCES 221 8 TEMPORARY SILICON-TETHERED
RING-CLOSING METATHESIS REACTIONS IN NATURAL PRODUCT SYNTHESIS 225 P.
ANDREW EVANS 8.1 INTRODUCTION 225 8.2 TEMPORARY SILICON-TETHERED
RING-CLOSING METATHESIS REACTIONS 226 8.2.1 O-SIR 2 -O TETHERED
SUBSTRATES: SYMMETRICAL SILAKETALS 226 8.2.1.1 C 2 -SYMMETRICA CONTENTS
XI 9 METATHESIS INVOLVING A RELAY AND APPLICATIONS IN NATURAL PRODUCT
SYNTHESIS 261 THOMAS R. HOYE AND JUNHA JEON 9.1 INTRODUCTION 261 9.1.1
THE RELAY CONCEPT 261 9.1.2 BASIC TENETS OF RCM 262 9.2 EARLY RELAY
METATHESIS DISCOVERIES 263 9.3 EXAMPLES OF RELAY METATHESIS DIRECTED AT
TARGETS OTHER THAN NATURAL PRODUCTS 268 9.4 EXAMPLES OF RELAY METATHESIS
MOTIVATED BY NATURAL PRODUCT SYNTHESIS 269 9.5 EXAMPLES OF RELAY
METATHESES THWARTED IN ACHIEVING THE DESIRED OUTCOME 278 9.5.1
INTERFERENCE FROM A TRUNCATION EVENT 278 9.5.2 INTERFERENCE FROM
PREMATURE MACROCYCLIZATION 279 9.6 CONCLUSION 281 ACKNOWLEDGMENTS 283
REFERENCES 283 10 CROSS-METATHESIS IN NATURAL PRODUCTS SYNTHESIS 287
JOELLE PRUNET AND LAURENCE GRIMAUD 10.1 INTRODUCTION 287 10.2
FUNCTIONALIZATION OF OLEFINS 287 10.2.1 CROSS-METATHESIS WITH ACRYLATE
DERIVATIVES 287 10.2.1.1 ACRYLONITRILE 287 10.2.1.2 THIOACRYLATES 288
10.2.1. XII CONTENTS 10.4 COUPLINGS 300 10.5 CASCADE PROCESSES INVOLVING
CM 303 10.5.1 ROM/CM 303 10.5.2 ROM/CM/RCM 305 10.5.3 ROM/RCM/CM 305
10.5.4 CM/RCM 306 10.5.5 RCEYM/CM 307 10.6 ENE-YNE CM 308 10.7 ALKYNE CM
309 10.8 CONCLUSION AND PERSPECTIVES 310 ACKNOWLEDGMENTS 310 REFERENCES
310 11 CASCADE METATHESIS IN NATURAL PRODUCT SYNTHESIS 313 MARTA PORTA
AND SIEGFRIED BLECHERT 11.1 INTRODUCTION 313 11.2 RCM-CM SEQUENCES 314
11.2.1 ENE-ENE RCM-CM 314 11.2.1.1 SYNTHESIS OF (3R,9IU0R)-PANAXYTRIOL
314 11.2.2 ENE-YNE-ENE RCM-CM 315 11.2.2.1 SYNTHESIS OF
(+)-8-EPI-XANTHATIN 316 11.3 ENE-YNE-ENE RCM-RCM 316 11.3.1 SYNTHESIS OF
BICYDIC STRUCTURES 317 11.3.1.1 SYNTHESIS OF (-)-SECURININE AND
(+)-VIROALLOSECURININE 317 11.3.1.2 TOTAL SYNTHESIS OF MT-LEPADIN F AND
G 318 11.3.2 SYNTHESIS OF TRICYCLIC COMPOUNDS 319 CONTENTS XIII 11.6
RCM-ROM SEQUENCES COMBINED WITH OTHER METATHESIS REACTIONS 332 11.6.1
RCM-ROM-RCM 332 11.6.1.1 RCM-ROM-RCM CASCADES OF MONOCYDIC STRUCTURES
333 11.6.1.2 RCM-ROM-RCM CASCADES OF BICYCLIC STRUCTURES 336 11.6.2
RCM-ROM-CM 337 11.6.2.1 SYNTHESIS OF (-)-LASUBINE II 337 11.6.2.2
SYNTHESIS OF (-T-)-CYLINDRAMIDE A AND BICYCLIC CORE OF GEODIN A 338
11.6.2.3 TOTAL SYNTHESIS OF (+)-MYCOEPOXYDIENE 338 11.7 CONCLUSIONS AND
OUTLOOK 339 REFERENCES 340 12 CATALYTIC ENANTIOSELECTIVE OLEFIN
METATHESIS AND NATURAL PRODUCT SYNTHESIS 343 AMIR H. HOVEYDA, STEVEN J.
MALCOLMSON, SIMON J. MEEK, AND ADII R. ZHUGRALIN 12.1 INTRODUCTION 343
12.2 TOTAL SYNTHESIS OF NATURAL PRODUCTS WITH ENANTIOMERICALLY PURE
CHIRAL OLEFIN METATHESIS CATALYSTS BEARING A CJ -SYMMETRIC DIOLATE
LIGAND 343 12.2.1 TOTAL SYNTHESIS OF CONIINE THROUGH ENANTIOSELECTIVE
RCM WITH SUBSTRATES BEARING A TERTIARY AMINE 343 12.2.2 ENANTIOSELECTIVE
SYNTHESIS OF AFRICANOL BY A RING-OPENING/RING-CLOSIN XIV I CONTENTS 13.8
CONCLUSION 369 ACKNOWLEDGMENTS 370 REFERENCES 370 INDEX 373 |
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| spelling | Metathesis in natural product synthesis strategies, substrates and catalysts ed. by Janine Cossy ... Weinheim Wiley-VCH 2010 XXVII, 384 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Naturstoff (DE-588)4041418-8 gnd rswk-swf Metathese Chemie (DE-588)4169656-6 gnd rswk-swf Metathese Chemie (DE-588)4169656-6 s Naturstoff (DE-588)4041418-8 s Chemische Synthese (DE-588)4133806-6 s DE-604 Cossy, Janine (DE-588)129680826 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3357028&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020326850&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Metathesis in natural product synthesis strategies, substrates and catalysts Chemische Synthese (DE-588)4133806-6 gnd Naturstoff (DE-588)4041418-8 gnd Metathese Chemie (DE-588)4169656-6 gnd |
| subject_GND | (DE-588)4133806-6 (DE-588)4041418-8 (DE-588)4169656-6 |
| title | Metathesis in natural product synthesis strategies, substrates and catalysts |
| title_auth | Metathesis in natural product synthesis strategies, substrates and catalysts |
| title_exact_search | Metathesis in natural product synthesis strategies, substrates and catalysts |
| title_full | Metathesis in natural product synthesis strategies, substrates and catalysts ed. by Janine Cossy ... |
| title_fullStr | Metathesis in natural product synthesis strategies, substrates and catalysts ed. by Janine Cossy ... |
| title_full_unstemmed | Metathesis in natural product synthesis strategies, substrates and catalysts ed. by Janine Cossy ... |
| title_short | Metathesis in natural product synthesis |
| title_sort | metathesis in natural product synthesis strategies substrates and catalysts |
| title_sub | strategies, substrates and catalysts |
| topic | Chemische Synthese (DE-588)4133806-6 gnd Naturstoff (DE-588)4041418-8 gnd Metathese Chemie (DE-588)4169656-6 gnd |
| topic_facet | Chemische Synthese Naturstoff Metathese Chemie |
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