Modern supramolecular chemistry: strategies for macrocycle synthesis
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| Format: | Book |
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| Language: | English |
| Published: |
Weinheim
WILEY-VCH
2008
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XVII, 400 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527318261 3527318267 |
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MARC
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| 020 | |a 3527318267 |c Gb. : ca. EUR 149.00 (freier Pr.), ca. sfr 235.00 (freier Pr.) |9 3-527-31826-7 | ||
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| 084 | |a CHE 780f |2 stub | ||
| 245 | 1 | 0 | |a Modern supramolecular chemistry |b strategies for macrocycle synthesis |c ed. by François Diederich ... |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2008 | |
| 300 | |a XVII, 400 S. |b Ill., graph. Darst. |c 240 mm x 170 mm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 7 | |a Supramoleculaire systemen |2 gtt | |
| 650 | 4 | |a Supramolecular chemistry | |
| 650 | 0 | 7 | |a Supramolekulare Chemie |0 (DE-588)4306141-2 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Supramolekulare Chemie |0 (DE-588)4306141-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Diederich, François |d 1952-2020 |e Sonstige |0 (DE-588)109354419 |4 oth | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe |z 978-3-527-62148-4 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe |z 978-3-527-62149-1 |
| 856 | 4 | 2 | |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=2974353&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
| 856 | 4 | 2 | |m OEBV Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016272562&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-016272562 | |
Record in the Search Index
| _version_ | 1805089794144862208 |
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| adam_text |
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* ****** ****** * * * **** **** * * * * * * * * * * * * ****** ********
* * * * * * * * CONTENTS PREFACE XIII* LIST OF CONTRIBUTORS XV*
BIOAETIVE MACROCYDIC PEPTIDES AND PEPTIDE MIMICS 1* ROB MJ. LISKAMP,
DIRK IS. RIJKERS, AND SASKIA E. BAKKER* I N T R O D U C T I O N 1 *
S E L E C T E D CYCLIC P E P T I D E S 4 * V A N C O M Y C I
N 4 * L A N T I B I O T I C : N I S I N 6 * C Y C L O S P
O R I N A 1 0 * C Y C L O T H E O N A M I D E A A N D
B 13* CYCLO RG D P E P T I D E S A S CXVSS3 A N T A G O N I S
T S 1 6 * S H 2 D O M A I N - B I N D I N G P E P T I D E S
1 9 * C O N C L U S I O N S 2 2 * E X P E R I M E N T A L :
S E L E C T E D P R O C E D U R E S 2 2 * S Y N T H E S I S
O F BICYCLIC P E P T I D E 9 : A N A L K E N E - B R I D
G E D M I M I C * O F T H E V A N C O M Y C I N C-D-E C A
V I T Y 2 2 * S Y N T H E S I S O F CYCLIC P E P T I D E
14 : A N A L K Y N E - B R I D G E D M I M I C * O F T H
E N I S I N A - R I N G F R A G M E N T 2 2 * R E F E R E
N C E S 2 5 * MACROCYDES BY RING-DOSURE METATHESIS 2 9 * JOELLE
PRUNET, ANDERSON ROUGE DOS SANTOS, ANDJEAN-PIERRE FIREZOU* I N T R O D U
C T I O N 2 9 * H O W T O C Y C L I Z E ? 3 2 * A T
H E R M O D Y N A M I C V E R S U S K I N E T I C I S S U E
3 2 * G E N E R A L E X P E R I M E N T A L C O N D I T I O N S
3 4 * I N F L U E N C E O F P O L A R C O M P L E X I N G
G R O U P S 3 5 * A D E C I S I V E F A C T O R F O R
S U C C E S S 3 5 * T H E T I T A N I U M T R I C K 3
6 * MODEM SUPRAMOLECULAR CHEMISTRY: STRATEGIES JOR MACROCYCLE
SYNTHESIS. E D I T E D BY FRANC;:OIS D I E D E R I C H , P E T E R
J. S L A N G , A N D RIK R. TYLCWINSKI C O P Y R I G H T
2 0 0 8 WILEY-VCH V E R L A G G M B H & CO. KGAA, W E I N H
E I M ISBN: 9 7 8 - 3 - 5 2 7 - 3 1 8 2 6 - 1 VI I CONTENTS
2.2.3.3 2.2.4 2.2.5 2.2.5.1 2.2.5.2 2.3 2.3.1 2.3.2 2.3.3 2.3.4 2.4 2.5
2.5.1 2.5.2 2.5.3 2.5.4 2.5.5 2.5.6 2.6 2.6.1 2.6.1.1 2.6.1.2 2.6.1.3
2.6.1.4 2.6.1.5 2.6.1.6 2.6.2 2.6.3 2.6.4 2.7 2.8 2.8.] 2.8.2 2.8.3
2.8.4 2.8.5 2.8.6 A PARTICULARLY FAVORABLE CASE: THE TEMPLATE-DIRECTED
RCM 37* SALICYLIHALAMIDES: INFLUENCE OF THE PHENOL PROTECTING*
SALICYLIHALAMIDES: INFLUENCE OF THE ALCOHOL- PROTECTING* SYNTHESIS OF
COMPOUND 16 (R=SIME2TBU) WITH CATALYST* CHEMOSELECTIVITY 37* SUBSTRATE
"TUNING" 38* CONFIGURATIONAL/CONFORMATIONAL ASPECT 38* INFLUENCE OF
FUNCTIONAL GROUP PROTEETION 39* FACTORS INFLUENCING THE DOUBLE-BOND
CONFIGURATION 39* A THERMODYNAMIC VERSUS KINETIC ISSUE 40* GENERAL
EXPERIMENTAL CONDITIONS 42* SUBSTRATE "TUNING" 42* SOLUTIONS 44* ENE-YNE
M-RCM 45* TANDEM PROCESSES LNVOLVING M-RCM 46* TANDEM CM/RCM 47* TANDEM
ROM/RCM 47* TANDEM RCM/ROM/RCM 48* RING-EXPANSION METATHESIS 48* OTHER
ONE-POT MULTISTEP PROCESSES 49* M-RCM AS PART OF MCR STRATEGIES 50*
REPRESENTATIVE SYNTHETIC APPLICATIONS 50* SALICYLIHALAMIDES/OXIMIDINES:
POTENT ANTITUMOR AGENTS* WITH SELECTIVE ANTI-V-ATPASE ACTIVITY 51*
SALICYLIHALAMIDES: LNFLUENCE OF THE CATALYST 52* GROUP 53* GROUP AT CU
54* SALICYLIHALAMIDES: LNFLUENCE OF THE NATURE* OF THE C15 SIDE CHAIN
54* SALICYLIHALAMIDES: MISCELLANEOUS 55* OXIMIDINES: USE OF RELAY
RING-CLOSING METATHESIS 55* RADICICOL-TYPE MACROLIDES: A PROMISING
FAMILY OF* ANTICANCER RESORCYLIDES 56* COLEOPHOMONES: A VERSATILE ACCESS
TO THIS CLASS OF* COMPLEX POLYCYCLIC DITERPENES 58* RCM IN
SUPRAMOLECULAR CHEMISTRY 59* CONCLUSION AND PERSPECTIVES 62*
EXPERIMENTAL: SELECTED PROCEDURES 62* SYNTHESIS OF COMPOUND 3 WITH
CATALYST S] 62* SYNTHESIS OF COMPOUND 6 WITH CATALYST GI 62* SYNTHESIS
OF COMPOUND 8 WITH CATALYST G2 63* GI/TI(OIPR)4 63* SYNTHESIS OF
COMPOUND 49 BY RCAM 63* SYNTHESIS OF COMPOUND 53 WITH GI BYENE-YNE RCM
63* REFERENCES 64* 3 3.1 3.2 3.3 3.4 3.5 3.5.1 3.5.2 4* 4.1 4.1.1 4.1.2
4.2 4.2.1 4.2.2 4.2.2.1 4.2.2.2 4.3 4.3.1 4.3.2 4.3.3 4.3.4 4.3.5 4.3.6
4.4 4.4.1 4.4.1.1 4.4.1.2 4.4.1.3 4.4.1.4 4.4.2 CONTENTS IVII*
SUPRAMOLECULAR MACROCYCLE SYNTHESIS BY H-BONDING ASSEMBLY 69* PABLO
BAI/ESTER AND JAVIER DE MENDOZA INTRODUCTION 69* STRATEGIES TO BUILD UP
SUPRAMOLECULAR MACROCYCLES BASED ON HYDROGEN BONDS 74* STRATEGIES TO
BUILD UP SUPRAMOLECULAR CAVITIES AND CAPSULES BASED ON HYDROGEN BONDS
90* SUMMARY AND OUTLOOK 105* EXPERIMENTAL: SELECTED PROCEDURES 106*
SOLID STATE FORMATION OF THE HEXAMERIC CAPSULE DERIVED FROM
PYROGALLOL[4]ARENE (50C) 106* CRYSTALS OFTHE HOST-GUEST ARRANGEMENT OF
52@(50B)6 106* REFERENCES 108* CUCURBIT[N]URILS 113* WEI-HAO HUANG,
SIMIN LIU, AND LYLE ISAACS INTRODUCTION 113* SYNTHESIS AND STRUCTURE OF
CUCURBIT[N]URIL HOMOLOGS* ALLOSTERIC CONTROL OF THE CONFORMATION OF A
CALIXL4]ARENE* EXPERIMENTAL SUPPORT FOR THE PROPOSED MECHANISM OF* S- TO
C-SHAPED ISOMERIZATION OF METHYLENE-BRIDGED* SYNTHESIS AND STRUCTURE OF
CUCURBIT[6]URIL AND* DECAMETHYLCUCURBIT[5]URIL 113* MOLECULAR
RECOGNITION PROPERTIES OFCUCURBIT[6]URIL 114* NEW MEMBERS OF THE
CUCURBIT[N]URIL FAMILY 115* PROPOSED MECHANISM OF CUCURBIT[N]URIL
FORMATION 115* (N = 5, 7, 8, 10) 116* REACTION CONDUCTED UNDER MILDER
CONDITIONS 116* CB[5] CAN BE RELEASED FROM CB[10].CB[5] TO YIELD* FREE
CUCURBIT[LO]URIL 117* APPLICATIONS OF MEMBERS OF THE CUCURBIT[N]URIL
FAMILY 118* PREPARATION OF MOLECULAR SWITCHES 118* SELF-ASSEMBLED
DENDRIMERS 119* PREPARATION OF MOLECULAR MACHINES 119* PREPARATION
OFCOMPLEX SELF-SORTING SYSTEMS 121* INSIDE CB[10] 122* AS A CARRIER OF
ANTI-CANCER AGENTS 123* CB[N] FORMATION 124* S-SHAPED AND C-SHAPED
METHYLENE-BRIDGED GLYCOLURIL DIMERS 124* SYNTHESIS OF METHYLENE-BRIDGED
GLYCOLURIL DIMERS 124* GLYCOLURIL DIMERS 126* MECHANISM OF S- TO
C-SHAPED ISOMERIZATION 126* IMPLICATIONS FOR THE SYNTHESIS OF
CUCURBIT[N]URIL* ANALOGS AND DERIVATIVES 128* BUILDING-BLOCK APPROACH TO
CUCURBIT[N]URIL ANALOGS 128* VIII I CONTENTS 4.4.3* BUILDING-BLOCK
APPROACH TO CUCURBIT[N]URIL DERIVATIVES 129* 4.4.4* IDENTIFICATION AND
ISOLATION OF INVERTED CUCURBIT[NJURILS (N = 6, 7) 130* 4.5* DIRECT
FUNCTIONALIZATION OF CUCURBIT[N]URILS 131* 4.5.1* PERHYDROXYLATION AND
FURTHER DERIVATIZATION OF CB[5J-CB[8] 131* 4.5.2* MULTIVALENT BINDING OF
SUGAR-DECORATED VESICLES TO LECTINS 132* 4.5.3* CUCURBIT[N]URIL-BASED
ARTIFICIAL ION CHANNELS 132* 4.6* NOR-SECO-CUCURBIT[10]URIL 133* 4.6.1*
DETECTION AND ISOLATION OF NOR-SECO-CUCURBIT[10JURIL 134* 4.6.2*
MOLECULAR RECOGNITION PROPERTIES OF NOR-SECO-CUCURBIT[LO]URIL 134* 4.7*
SUMMARY AND CONCLUSIONS 135* 4.8* EXPERIMENTAL: SELECTED PROCEDURES 137*
4.8.1* SYNTHESIS OF GLYCOLURILS 137* 4.8.2* SYNTHESIS AND SEPARATION OF
CUCURBIT[N]URILS 138* 4.8.3* SYNTHESIS OF NOR-SECO-CUCURBIT[10]URIL 140*
REFERENCES 141* 5* TETRA-UREA CALIX[4]ARENES - FROM DIMERIC CAPSULES* TO
NOVEL CATENANES AND ROTAXANES 143* CANNA PODOPRYGORINA AND VOLKER BOEHMER
5.1* [NTRODUCTION 143* 5.2* BASICS OFTETRA-UREA CALIXL4JARENES 148*
5.2.1* SYNTHESIS 148* 5.2.2* DIMERIC CAPSULES 149* 5.2.3* HETERODIMERS
151* 5.2.4* SYMMETRY PROPERTIES 152* 5.3* PREORGANIZATION IN DIMERS
OFTETRA-UREA CALIX[4]ARENES 153* 5.3.1* GENERAL CONSIDERATIONS 153*
5.3.2* FIRST ATTEMPTS 154* 5.4* MULTIMACROCYCLES 155* 5.4.1* TEMPLATE
SYNTHESIS OFMULTIMACROCYCLIC CALIX[4]ARENES 155* 5.4.2* DOUBLE TEMPLATE
SYNTHESIS OFGIANT MACROCYCLES 160* 5.5* MULTIPLE CATENANES BASED ON
CALIX[4]ARENES 162* 5.5.1* GENERAL CONSIDERATIONS 162* 5.5.2*
BIS[2JCATENANES 163* 5.5.3* TOWARDS NOVEL TOPOLOGIES 166* 5.5.4*
BIS[3]CATENANES AND CYCLIC [8]CATENANES 168* 5.6* MULTIPLE ROTAXANES
170* 5.7* SELF-SORTING AND FORMATION OF LARGER ASSEMBLIES 172* 5.8*
CONCLUSIONS AND OUTLOOK 176* 5.9* EXPERIMENTAL: SELECTED PROCEDURES 177*
5.9.1* SYNTHESIS OFTETRA-UREA 5 (Y = CSH LL : M = 9) 177* 5.9.2*
SYNTHESIS OF BISLOOP TETRA-UREA 8 (Y = CSH LL : N = 20) 177* 5.9.3*
SYNTHESIS OF BIS[2JCATENANE 12 (Y = CSH LL; N = 20) 177* 5.9.4*
SYNTHESIS OFTETRA-UREA 6A (Y = CSH LL ; M = 6) 178* 5.9.5* SYNTHESIS
OFTETRALOOP TETRA-UREA 9 (Y = CSH LL ; N = 14) 178* CONTENTS IIX* 5.9.6
6* 6.1 6.1.1 6.1.2 6.2 6.2.1 6.2.2 6.2.3 6.2.3.1 6.2.3.2 6.2.3.3 6.3 6.4
6.4.1 6.4.2 6.4.3 6.4.4 6.4.5 6.4.6 6.4.7 7* 7.1 7.2 7.2.1 7.2.2 7.2.2.1
7.2.2.2 7.2.3 7.2.4 7.2.5 7.3 7.4 7.4.1 7.4.2 7.4.3 7.4.4 7.4.5
SYNTHESIS OF [8]CATENANE 14 (Y = CSH LL ; N = 14) 179* REFERENCES 180*
SHAPE-PERSISTENT MACROCYCLES BASED ON ACETYLENIC SCAFFOLDING 185* AMBER
L. SADOWY AND RIK R. TYKWINSKI* INTRODUCTION 185* SPM SYNTHESIS THROUGH
INTERMOLECULAR REACTIONS 186* SPM SYNTHESIS THROUGH INTRAMOLECULAR
REACTIONS 190* SUPRAMOLECULAR SPMS 194* SPMS AS COMPONENTS IN
SUPRAMOLECULAR ASSEMBLIES 195* SPMS IN HOST-GUEST SYSTEMS 203*
AGGREGATION AND SURFACE CHEMISTRY OF SPMS 208* AGGREGATION OF SPMS 209*
LIQUID-CRYSTALLINE SPMS 215* ADSORPTION OF SPMS ON SURFACES 218*
CONC1USIONS 224* EXPERIMENTAL: SELECTED PROCEDURES 224* SPM 13:
PD-CATALYZED CADIOT-CHODKIEWICZ CONDITIONS 224* SPM 19: USE OF
ARYLTRIAZENE AS A MASKING GROUP FAR ARYL IODIDES 224* SPM 20: EGLINTON
CONDITIONS 225* SPM 33: HAY CONDITIONS 225* PRE-CATENANE 56: BRESLOW
CONDITIONS 225* SPM 91: SCHIFF-BASE CONDENSATION CONDITIONS 226*
LARGE-SCALE SYNTHESIS OF SPM 124 VIA AN ALKYNE METATHESIS 226*
REFERENCES 228* SUPRAMOLECULAR 3D ARCHITECTURES BY METAL-DIRECTED
ASSEMBLY* OF SYNTHETIC MACROCYCLES 233* LAURA PIRONDINI AND ENRICO
DALCANALE INTRODUCTION 233* COORDINATION CAGES 234* DIMERIC
CALIXARENE-BASED COORDINATION CAGES 235* CAVITAND-BASED DIMERIC
COORDINATION CAGES 236* THE APICAL FUNCTIONALIZATION APPROACH 236*
INTRODUCTION OF THE LIGANDS AS BRIDGING UNITS 248* TRIMERIC, TETRAMERIC,
AND HEXAMERIC COORDINATION CAGES 252* SELF-ASSEMBLY OF COORDINATION
CAGES ON SURFACES 255* SELF-ASSEMBLY OF MULTITOPIC MACROCYC1IC COMPLEXES
263* CONC1USION 271* EXPERIMENTAL: SELECTED PROCEDURES 272*
TETRAPICOLYL-BRIDGED CAVITAND 31A 272* TETRACYANO CAVITAND 40 272*
AC-DIBRIDGED TOLYLPYRIDYL CAVITAND 35 272* JAC-BR(COHRE AC DITOPIC
CAVITAND COMPLEX 36 273* TETRATOPIC CAVITAND COMPLEX 48 273* REFERENCES
274* X I CONTENTS 8* 8.1 8.2 8.2.1 8.2.2 8.3 8.3.1 8.3.2 8.3.3 8.3.4
8.3.5 8.3.6 8.3.7 8.4 8.4.1 8.4.2 8.5 8.5.1 8.5.2 8.5.3 8.5.4 8.5.5
8.5.6 8.5.7 8.6 8.7 9* 9.1 9.2 9.2.1 9.2.2 9.2.3 9.2.4 9.2.5 9.3 9.4 9.5
9.5.1 9.5.2 NEW PROPERTIES AND REACTIONS IN SELF-ASSEMBLED* M 6 L 4
COORDINATION CAGES 277* MAKOTO FUJITA AND MICHITO YOSHIZAWA INTRODUCTION
277* SELF-ASSEMBLY OF HOLLOW COMPLEXES 278* M64 OCTAHEDRAL COMPLEX 280*
LARGE-SCALE PRODUCTION OF THE M64 COMPLEX 280* INCLUSION PROPERTIES 288*
INCLUSION OF ADAMANTANE AND CARBORANE 288* INCLUSION GEOMETRY 289*
BIMOLECULAR RECOGNITION 291* RECOGNITION OF BULKY GUESTS 293* THE
RECOGNITION OF AZOBENZENE AND STILBENE 295* MOLECULAR ICE 296* PEPTIDE
RECOGNITION 297* NEW PHYSICAL PROPERTIES 299* REDOX CONTROL OF FERROCENE
299* INDUCTION OF INTERMOLECULAR SPIN-SPIN INTERACTION 299* NEW
REACTIONS 301* [2+2] OLEFIN PHOTODIMERIZATION 302* PAIRWISE-SELECTIVE
OLEFIN PHOTODIMERIZATION 303* UNUSUAL [2+2J PHOTOADDITION 303*
DIELS-ALDER REACTION 303* ALKANE OXIDATION 306* WACKER OXIDATION 306*
DISCRETE SILOXANE SYNTHESIS 308* CONCLUSION 308* EXPERIMENTAL: SYNTHESIS
OF M64 CAGE 2 309* REFERENCES 309* ANION-BINDING MACROCYCLES 315* EVGENY
A. KATAYEV, PATRICIA J. MELFI, ANDJONATHAN L. SESS/ER* INTRODUCTION 315*
DITOPIC RECEPTORS AND RECEPTORS FAR ION PAIRS 317* CROWN COMPLEXES 318*
CALIXARENES 321* CHOLAPODS 325* PYRROLES 326* MISCELLANEOUS 330*
RECEPTORS WITH DIFFERENT BINDING SITES 332* CONCLUSIONS 341*
EXPERIMENTAL: SELECTED PROCEDURES 342* MACROCYCLE H 2S04.53 342*
MACROCYCLE 55 342* REFERENCES 343* CONTENTS IXI* 10 10.1 10.1.1 10.2
10.2.1 10.2.2 10.2.3 10.2.4 10.2.5 10.2.6 10.2.7 10.3 10.4 10.4.1 10.4.2
10.4.3 10.4.4 ROTAXANE AND CATENANE SYNTHESIS 349* JAMES A. WISNER AND
BARRY A. BLIGHT* LNTRODUCTION 349* GENERAL COMMENTS 349*
MACROCYCLIZATION REACTIONS RESULTING IN INTERLOCKED PRODUCTS 351*
WILLIAMSON ETHER SYNTHESIS 351* QUATERNIZATION OF AROMATIC AMINES
(MENSCHUTKIN REACTION) 351* CONDENSATION OFAMINES WITH ACID CHLORIDES
354* OXIDATIVE ACETYLIDE COUPLING 361* ALKENE METATHESIS 366* IMINE
FORMATIONJREDUCTIVE AMINATION 374* METAL-LIGAND COORDINATION 379*
CONCLUSIONS 384* EXPERIMENTAL: SELECTED PROCEDURES 384* [2]CATENANE 14
384* [2JCATENANE 25 386* [2]ROTAXANE 81 386* [2]CATENANE 118 386*
REFERENCES 387* INDEX 393* |
| adam_txt |
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* ****** ****** * * * **** **** * * * * * * * * * * * * ****** ********
* * * * * * * * CONTENTS PREFACE XIII* LIST OF CONTRIBUTORS XV*
BIOAETIVE MACROCYDIC PEPTIDES AND PEPTIDE MIMICS 1* ROB MJ. LISKAMP,
DIRK IS. RIJKERS, AND SASKIA E. BAKKER* I N T R O D U C T I O N 1 *
S E L E C T E D CYCLIC P E P T I D E S 4 * V A N C O M Y C I
N 4 * L A N T I B I O T I C : N I S I N 6 * C Y C L O S P
O R I N A 1 0 * C Y C L O T H E O N A M I D E A A N D
B 13* CYCLO RG D P E P T I D E S A S CXVSS3 A N T A G O N I S
T S 1 6 * S H 2 D O M A I N - B I N D I N G P E P T I D E S
1 9 * C O N C L U S I O N S 2 2 * E X P E R I M E N T A L :
S E L E C T E D P R O C E D U R E S 2 2 * S Y N T H E S I S
O F BICYCLIC P E P T I D E 9 : A N A L K E N E - B R I D
G E D M I M I C * O F T H E V A N C O M Y C I N C-D-E C A
V I T Y 2 2 * S Y N T H E S I S O F CYCLIC P E P T I D E
14 : A N A L K Y N E - B R I D G E D M I M I C * O F T H
E N I S I N A - R I N G F R A G M E N T 2 2 * R E F E R E
N C E S 2 5 * MACROCYDES BY RING-DOSURE METATHESIS 2 9 * JOELLE
PRUNET, ANDERSON ROUGE DOS SANTOS, ANDJEAN-PIERRE FIREZOU* I N T R O D U
C T I O N 2 9 * H O W T O C Y C L I Z E ? 3 2 * A T
H E R M O D Y N A M I C V E R S U S K I N E T I C I S S U E
3 2 * G E N E R A L E X P E R I M E N T A L C O N D I T I O N S
3 4 * I N F L U E N C E O F P O L A R C O M P L E X I N G
G R O U P S 3 5 * A D E C I S I V E F A C T O R F O R
S U C C E S S 3 5 * T H E T I T A N I U M T R I C K 3
6 * MODEM SUPRAMOLECULAR CHEMISTRY: STRATEGIES JOR MACROCYCLE
SYNTHESIS. E D I T E D BY FRANC;:OIS D I E D E R I C H , P E T E R
J. S L A N G , A N D RIK R. TYLCWINSKI C O P Y R I G H T
2 0 0 8 WILEY-VCH V E R L A G G M B H & CO. KGAA, W E I N H
E I M ISBN: 9 7 8 - 3 - 5 2 7 - 3 1 8 2 6 - 1 VI I CONTENTS
2.2.3.3 2.2.4 2.2.5 2.2.5.1 2.2.5.2 2.3 2.3.1 2.3.2 2.3.3 2.3.4 2.4 2.5
2.5.1 2.5.2 2.5.3 2.5.4 2.5.5 2.5.6 2.6 2.6.1 2.6.1.1 2.6.1.2 2.6.1.3
2.6.1.4 2.6.1.5 2.6.1.6 2.6.2 2.6.3 2.6.4 2.7 2.8 2.8.] 2.8.2 2.8.3
2.8.4 2.8.5 2.8.6 A PARTICULARLY FAVORABLE CASE: THE TEMPLATE-DIRECTED
RCM 37* SALICYLIHALAMIDES: INFLUENCE OF THE PHENOL PROTECTING*
SALICYLIHALAMIDES: INFLUENCE OF THE ALCOHOL- PROTECTING* SYNTHESIS OF
COMPOUND 16 (R=SIME2TBU) WITH CATALYST* CHEMOSELECTIVITY 37* SUBSTRATE
"TUNING" 38* CONFIGURATIONAL/CONFORMATIONAL ASPECT 38* INFLUENCE OF
FUNCTIONAL GROUP PROTEETION 39* FACTORS INFLUENCING THE DOUBLE-BOND
CONFIGURATION 39* A THERMODYNAMIC VERSUS KINETIC ISSUE 40* GENERAL
EXPERIMENTAL CONDITIONS 42* SUBSTRATE "TUNING" 42* SOLUTIONS 44* ENE-YNE
M-RCM 45* TANDEM PROCESSES LNVOLVING M-RCM 46* TANDEM CM/RCM 47* TANDEM
ROM/RCM 47* TANDEM RCM/ROM/RCM 48* RING-EXPANSION METATHESIS 48* OTHER
ONE-POT MULTISTEP PROCESSES 49* M-RCM AS PART OF MCR STRATEGIES 50*
REPRESENTATIVE SYNTHETIC APPLICATIONS 50* SALICYLIHALAMIDES/OXIMIDINES:
POTENT ANTITUMOR AGENTS* WITH SELECTIVE ANTI-V-ATPASE ACTIVITY 51*
SALICYLIHALAMIDES: LNFLUENCE OF THE CATALYST 52* GROUP 53* GROUP AT CU
54* SALICYLIHALAMIDES: LNFLUENCE OF THE NATURE* OF THE C15 SIDE CHAIN
54* SALICYLIHALAMIDES: MISCELLANEOUS 55* OXIMIDINES: USE OF RELAY
RING-CLOSING METATHESIS 55* RADICICOL-TYPE MACROLIDES: A PROMISING
FAMILY OF* ANTICANCER RESORCYLIDES 56* COLEOPHOMONES: A VERSATILE ACCESS
TO THIS CLASS OF* COMPLEX POLYCYCLIC DITERPENES 58* RCM IN
SUPRAMOLECULAR CHEMISTRY 59* CONCLUSION AND PERSPECTIVES 62*
EXPERIMENTAL: SELECTED PROCEDURES 62* SYNTHESIS OF COMPOUND 3 WITH
CATALYST S] 62* SYNTHESIS OF COMPOUND 6 WITH CATALYST GI 62* SYNTHESIS
OF COMPOUND 8 WITH CATALYST G2 63* GI/TI(OIPR)4 63* SYNTHESIS OF
COMPOUND 49 BY RCAM 63* SYNTHESIS OF COMPOUND 53 WITH GI BYENE-YNE RCM
63* REFERENCES 64* 3 3.1 3.2 3.3 3.4 3.5 3.5.1 3.5.2 4* 4.1 4.1.1 4.1.2
4.2 4.2.1 4.2.2 4.2.2.1 4.2.2.2 4.3 4.3.1 4.3.2 4.3.3 4.3.4 4.3.5 4.3.6
4.4 4.4.1 4.4.1.1 4.4.1.2 4.4.1.3 4.4.1.4 4.4.2 CONTENTS IVII*
SUPRAMOLECULAR MACROCYCLE SYNTHESIS BY H-BONDING ASSEMBLY 69* PABLO
BAI/ESTER AND JAVIER DE MENDOZA INTRODUCTION 69* STRATEGIES TO BUILD UP
SUPRAMOLECULAR MACROCYCLES BASED ON HYDROGEN BONDS 74* STRATEGIES TO
BUILD UP SUPRAMOLECULAR CAVITIES AND CAPSULES BASED ON HYDROGEN BONDS
90* SUMMARY AND OUTLOOK 105* EXPERIMENTAL: SELECTED PROCEDURES 106*
SOLID STATE FORMATION OF THE HEXAMERIC CAPSULE DERIVED FROM
PYROGALLOL[4]ARENE (50C) 106* CRYSTALS OFTHE HOST-GUEST ARRANGEMENT OF
52@(50B)6 106* REFERENCES 108* CUCURBIT[N]URILS 113* WEI-HAO HUANG,
SIMIN LIU, AND LYLE ISAACS INTRODUCTION 113* SYNTHESIS AND STRUCTURE OF
CUCURBIT[N]URIL HOMOLOGS* ALLOSTERIC CONTROL OF THE CONFORMATION OF A
CALIXL4]ARENE* EXPERIMENTAL SUPPORT FOR THE PROPOSED MECHANISM OF* S- TO
C-SHAPED ISOMERIZATION OF METHYLENE-BRIDGED* SYNTHESIS AND STRUCTURE OF
CUCURBIT[6]URIL AND* DECAMETHYLCUCURBIT[5]URIL 113* MOLECULAR
RECOGNITION PROPERTIES OFCUCURBIT[6]URIL 114* NEW MEMBERS OF THE
CUCURBIT[N]URIL FAMILY 115* PROPOSED MECHANISM OF CUCURBIT[N]URIL
FORMATION 115* (N = 5, 7, 8, 10) 116* REACTION CONDUCTED UNDER MILDER
CONDITIONS 116* CB[5] CAN BE RELEASED FROM CB[10].CB[5] TO YIELD* FREE
CUCURBIT[LO]URIL 117* APPLICATIONS OF MEMBERS OF THE CUCURBIT[N]URIL
FAMILY 118* PREPARATION OF MOLECULAR SWITCHES 118* SELF-ASSEMBLED
DENDRIMERS 119* PREPARATION OF MOLECULAR MACHINES 119* PREPARATION
OFCOMPLEX SELF-SORTING SYSTEMS 121* INSIDE CB[10] 122* AS A CARRIER OF
ANTI-CANCER AGENTS 123* CB[N] FORMATION 124* S-SHAPED AND C-SHAPED
METHYLENE-BRIDGED GLYCOLURIL DIMERS 124* SYNTHESIS OF METHYLENE-BRIDGED
GLYCOLURIL DIMERS 124* GLYCOLURIL DIMERS 126* MECHANISM OF S- TO
C-SHAPED ISOMERIZATION 126* IMPLICATIONS FOR THE SYNTHESIS OF
CUCURBIT[N]URIL* ANALOGS AND DERIVATIVES 128* BUILDING-BLOCK APPROACH TO
CUCURBIT[N]URIL ANALOGS 128* VIII I CONTENTS 4.4.3* BUILDING-BLOCK
APPROACH TO CUCURBIT[N]URIL DERIVATIVES 129* 4.4.4* IDENTIFICATION AND
ISOLATION OF INVERTED CUCURBIT[NJURILS (N = 6, 7) 130* 4.5* DIRECT
FUNCTIONALIZATION OF CUCURBIT[N]URILS 131* 4.5.1* PERHYDROXYLATION AND
FURTHER DERIVATIZATION OF CB[5J-CB[8] 131* 4.5.2* MULTIVALENT BINDING OF
SUGAR-DECORATED VESICLES TO LECTINS 132* 4.5.3* CUCURBIT[N]URIL-BASED
ARTIFICIAL ION CHANNELS 132* 4.6* NOR-SECO-CUCURBIT[10]URIL 133* 4.6.1*
DETECTION AND ISOLATION OF NOR-SECO-CUCURBIT[10JURIL 134* 4.6.2*
MOLECULAR RECOGNITION PROPERTIES OF NOR-SECO-CUCURBIT[LO]URIL 134* 4.7*
SUMMARY AND CONCLUSIONS 135* 4.8* EXPERIMENTAL: SELECTED PROCEDURES 137*
4.8.1* SYNTHESIS OF GLYCOLURILS 137* 4.8.2* SYNTHESIS AND SEPARATION OF
CUCURBIT[N]URILS 138* 4.8.3* SYNTHESIS OF NOR-SECO-CUCURBIT[10]URIL 140*
REFERENCES 141* 5* TETRA-UREA CALIX[4]ARENES - FROM DIMERIC CAPSULES* TO
NOVEL CATENANES AND ROTAXANES 143* CANNA PODOPRYGORINA AND VOLKER BOEHMER
5.1* [NTRODUCTION 143* 5.2* BASICS OFTETRA-UREA CALIXL4JARENES 148*
5.2.1* SYNTHESIS 148* 5.2.2* DIMERIC CAPSULES 149* 5.2.3* HETERODIMERS
151* 5.2.4* SYMMETRY PROPERTIES 152* 5.3* PREORGANIZATION IN DIMERS
OFTETRA-UREA CALIX[4]ARENES 153* 5.3.1* GENERAL CONSIDERATIONS 153*
5.3.2* FIRST ATTEMPTS 154* 5.4* MULTIMACROCYCLES 155* 5.4.1* TEMPLATE
SYNTHESIS OFMULTIMACROCYCLIC CALIX[4]ARENES 155* 5.4.2* DOUBLE TEMPLATE
SYNTHESIS OFGIANT MACROCYCLES 160* 5.5* MULTIPLE CATENANES BASED ON
CALIX[4]ARENES 162* 5.5.1* GENERAL CONSIDERATIONS 162* 5.5.2*
BIS[2JCATENANES 163* 5.5.3* TOWARDS NOVEL TOPOLOGIES 166* 5.5.4*
BIS[3]CATENANES AND CYCLIC [8]CATENANES 168* 5.6* MULTIPLE ROTAXANES
170* 5.7* SELF-SORTING AND FORMATION OF LARGER ASSEMBLIES 172* 5.8*
CONCLUSIONS AND OUTLOOK 176* 5.9* EXPERIMENTAL: SELECTED PROCEDURES 177*
5.9.1* SYNTHESIS OFTETRA-UREA 5 (Y = CSH LL : M = 9) 177* 5.9.2*
SYNTHESIS OF BISLOOP TETRA-UREA 8 (Y = CSH LL : N = 20) 177* 5.9.3*
SYNTHESIS OF BIS[2JCATENANE 12 (Y = CSH LL; N = 20) 177* 5.9.4*
SYNTHESIS OFTETRA-UREA 6A (Y = CSH LL ; M = 6) 178* 5.9.5* SYNTHESIS
OFTETRALOOP TETRA-UREA 9 (Y = CSH LL ; N = 14) 178* CONTENTS IIX* 5.9.6
6* 6.1 6.1.1 6.1.2 6.2 6.2.1 6.2.2 6.2.3 6.2.3.1 6.2.3.2 6.2.3.3 6.3 6.4
6.4.1 6.4.2 6.4.3 6.4.4 6.4.5 6.4.6 6.4.7 7* 7.1 7.2 7.2.1 7.2.2 7.2.2.1
7.2.2.2 7.2.3 7.2.4 7.2.5 7.3 7.4 7.4.1 7.4.2 7.4.3 7.4.4 7.4.5
SYNTHESIS OF [8]CATENANE 14 (Y = CSH LL ; N = 14) 179* REFERENCES 180*
SHAPE-PERSISTENT MACROCYCLES BASED ON ACETYLENIC SCAFFOLDING 185* AMBER
L. SADOWY AND RIK R. TYKWINSKI* INTRODUCTION 185* SPM SYNTHESIS THROUGH
INTERMOLECULAR REACTIONS 186* SPM SYNTHESIS THROUGH INTRAMOLECULAR
REACTIONS 190* SUPRAMOLECULAR SPMS 194* SPMS AS COMPONENTS IN
SUPRAMOLECULAR ASSEMBLIES 195* SPMS IN HOST-GUEST SYSTEMS 203*
AGGREGATION AND SURFACE CHEMISTRY OF SPMS 208* AGGREGATION OF SPMS 209*
LIQUID-CRYSTALLINE SPMS 215* ADSORPTION OF SPMS ON SURFACES 218*
CONC1USIONS 224* EXPERIMENTAL: SELECTED PROCEDURES 224* SPM 13:
PD-CATALYZED CADIOT-CHODKIEWICZ CONDITIONS 224* SPM 19: USE OF
ARYLTRIAZENE AS A MASKING GROUP FAR ARYL IODIDES 224* SPM 20: EGLINTON
CONDITIONS 225* SPM 33: HAY CONDITIONS 225* PRE-CATENANE 56: BRESLOW
CONDITIONS 225* SPM 91: SCHIFF-BASE CONDENSATION CONDITIONS 226*
LARGE-SCALE SYNTHESIS OF SPM 124 VIA AN ALKYNE METATHESIS 226*
REFERENCES 228* SUPRAMOLECULAR 3D ARCHITECTURES BY METAL-DIRECTED
ASSEMBLY* OF SYNTHETIC MACROCYCLES 233* LAURA PIRONDINI AND ENRICO
DALCANALE INTRODUCTION 233* COORDINATION CAGES 234* DIMERIC
CALIXARENE-BASED COORDINATION CAGES 235* CAVITAND-BASED DIMERIC
COORDINATION CAGES 236* THE APICAL FUNCTIONALIZATION APPROACH 236*
INTRODUCTION OF THE LIGANDS AS BRIDGING UNITS 248* TRIMERIC, TETRAMERIC,
AND HEXAMERIC COORDINATION CAGES 252* SELF-ASSEMBLY OF COORDINATION
CAGES ON SURFACES 255* SELF-ASSEMBLY OF MULTITOPIC MACROCYC1IC COMPLEXES
263* CONC1USION 271* EXPERIMENTAL: SELECTED PROCEDURES 272*
TETRAPICOLYL-BRIDGED CAVITAND 31A 272* TETRACYANO CAVITAND 40 272*
AC-DIBRIDGED TOLYLPYRIDYL CAVITAND 35 272* JAC-BR(COHRE AC DITOPIC
CAVITAND COMPLEX 36 273* TETRATOPIC CAVITAND COMPLEX 48 273* REFERENCES
274* X I CONTENTS 8* 8.1 8.2 8.2.1 8.2.2 8.3 8.3.1 8.3.2 8.3.3 8.3.4
8.3.5 8.3.6 8.3.7 8.4 8.4.1 8.4.2 8.5 8.5.1 8.5.2 8.5.3 8.5.4 8.5.5
8.5.6 8.5.7 8.6 8.7 9* 9.1 9.2 9.2.1 9.2.2 9.2.3 9.2.4 9.2.5 9.3 9.4 9.5
9.5.1 9.5.2 NEW PROPERTIES AND REACTIONS IN SELF-ASSEMBLED* M 6 L 4
COORDINATION CAGES 277* MAKOTO FUJITA AND MICHITO YOSHIZAWA INTRODUCTION
277* SELF-ASSEMBLY OF HOLLOW COMPLEXES 278* M64 OCTAHEDRAL COMPLEX 280*
LARGE-SCALE PRODUCTION OF THE M64 COMPLEX 280* INCLUSION PROPERTIES 288*
INCLUSION OF ADAMANTANE AND CARBORANE 288* INCLUSION GEOMETRY 289*
BIMOLECULAR RECOGNITION 291* RECOGNITION OF BULKY GUESTS 293* THE
RECOGNITION OF AZOBENZENE AND STILBENE 295* MOLECULAR ICE 296* PEPTIDE
RECOGNITION 297* NEW PHYSICAL PROPERTIES 299* REDOX CONTROL OF FERROCENE
299* INDUCTION OF INTERMOLECULAR SPIN-SPIN INTERACTION 299* NEW
REACTIONS 301* [2+2] OLEFIN PHOTODIMERIZATION 302* PAIRWISE-SELECTIVE
OLEFIN PHOTODIMERIZATION 303* UNUSUAL [2+2J PHOTOADDITION 303*
DIELS-ALDER REACTION 303* ALKANE OXIDATION 306* WACKER OXIDATION 306*
DISCRETE SILOXANE SYNTHESIS 308* CONCLUSION 308* EXPERIMENTAL: SYNTHESIS
OF M64 CAGE 2 309* REFERENCES 309* ANION-BINDING MACROCYCLES 315* EVGENY
A. KATAYEV, PATRICIA J. MELFI, ANDJONATHAN L. SESS/ER* INTRODUCTION 315*
DITOPIC RECEPTORS AND RECEPTORS FAR ION PAIRS 317* CROWN COMPLEXES 318*
CALIXARENES 321* CHOLAPODS 325* PYRROLES 326* MISCELLANEOUS 330*
RECEPTORS WITH DIFFERENT BINDING SITES 332* CONCLUSIONS 341*
EXPERIMENTAL: SELECTED PROCEDURES 342* MACROCYCLE H 2S04.53 342*
MACROCYCLE 55 342* REFERENCES 343* CONTENTS IXI* 10 10.1 10.1.1 10.2
10.2.1 10.2.2 10.2.3 10.2.4 10.2.5 10.2.6 10.2.7 10.3 10.4 10.4.1 10.4.2
10.4.3 10.4.4 ROTAXANE AND CATENANE SYNTHESIS 349* JAMES A. WISNER AND
BARRY A. BLIGHT* LNTRODUCTION 349* GENERAL COMMENTS 349*
MACROCYCLIZATION REACTIONS RESULTING IN INTERLOCKED PRODUCTS 351*
WILLIAMSON ETHER SYNTHESIS 351* QUATERNIZATION OF AROMATIC AMINES
(MENSCHUTKIN REACTION) 351* CONDENSATION OFAMINES WITH ACID CHLORIDES
354* OXIDATIVE ACETYLIDE COUPLING 361* ALKENE METATHESIS 366* IMINE
FORMATIONJREDUCTIVE AMINATION 374* METAL-LIGAND COORDINATION 379*
CONCLUSIONS 384* EXPERIMENTAL: SELECTED PROCEDURES 384* [2]CATENANE 14
384* [2JCATENANE 25 386* [2]ROTAXANE 81 386* [2]CATENANE 118 386*
REFERENCES 387* INDEX 393* |
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| illustrated | Illustrated |
| index_date | 2024-07-02T19:32:22Z |
| indexdate | 2024-07-20T09:29:35Z |
| institution | BVB |
| isbn | 9783527318261 3527318267 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016272562 |
| oclc_num | 166378356 |
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| owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-29T DE-526 DE-83 DE-11 |
| physical | XVII, 400 S. Ill., graph. Darst. 240 mm x 170 mm |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Modern supramolecular chemistry strategies for macrocycle synthesis ed. by François Diederich ... Weinheim WILEY-VCH 2008 XVII, 400 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Supramoleculaire systemen gtt Supramolecular chemistry Supramolekulare Chemie (DE-588)4306141-2 gnd rswk-swf Supramolekulare Chemie (DE-588)4306141-2 s DE-604 Diederich, François 1952-2020 Sonstige (DE-588)109354419 oth Erscheint auch als Online-Ausgabe 978-3-527-62148-4 Erscheint auch als Online-Ausgabe 978-3-527-62149-1 text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2974353&prov=M&dok_var=1&dok_ext=htm Inhaltstext OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016272562&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern supramolecular chemistry strategies for macrocycle synthesis Supramoleculaire systemen gtt Supramolecular chemistry Supramolekulare Chemie (DE-588)4306141-2 gnd |
| subject_GND | (DE-588)4306141-2 |
| title | Modern supramolecular chemistry strategies for macrocycle synthesis |
| title_auth | Modern supramolecular chemistry strategies for macrocycle synthesis |
| title_exact_search | Modern supramolecular chemistry strategies for macrocycle synthesis |
| title_exact_search_txtP | Modern supramolecular chemistry strategies for macrocycle synthesis |
| title_full | Modern supramolecular chemistry strategies for macrocycle synthesis ed. by François Diederich ... |
| title_fullStr | Modern supramolecular chemistry strategies for macrocycle synthesis ed. by François Diederich ... |
| title_full_unstemmed | Modern supramolecular chemistry strategies for macrocycle synthesis ed. by François Diederich ... |
| title_short | Modern supramolecular chemistry |
| title_sort | modern supramolecular chemistry strategies for macrocycle synthesis |
| title_sub | strategies for macrocycle synthesis |
| topic | Supramoleculaire systemen gtt Supramolecular chemistry Supramolekulare Chemie (DE-588)4306141-2 gnd |
| topic_facet | Supramoleculaire systemen Supramolecular chemistry Supramolekulare Chemie |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=2974353&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016272562&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT diederichfrancois modernsupramolecularchemistrystrategiesformacrocyclesynthesis |