Organic Synthesis Today and Tomorrow (eBook)

Proceedings of the 3rd IUPAC Symposium on Organic Synthesis, Madison, Wisconsin, USA, 15-20 June 1980

C. Richard Hutchinson, Barry M. Trost (Herausgeber)

eBook Download: PDF

2017 | 1. Auflage
364 Seiten
Elsevier Science (Verlag)
978-1-4831-5466-4 (ISBN)

Infos

Organic Synthesis: Today and Tomorrow covers the proceedings of the Third International Union of Pure and Applied Chemistry (IUPAC) Symposium on Organic Synthesis. The book covers topics that tackle relevant issues about organic chemistry. Comprised of 27 chapters, the book covers lectures that tackle topics pertaining organic chemistry. These topics include useful synthetic methods for general application; development of chemistry concepts for use in construction of molecular sub-assemblies; and interplay of synthetic methodology and the total synthesis of organic compounds. The book will be of great interest to scientists, such as biochemists who are concerned with the advances in organic chemistry.

Inhalt

Front Cover 1
Organic Synthesis Today and Tomorrow 4
Copyright 5
Table of Contents 
6 
Organizing Committee 8
PREFACE 10
ACKNOWLEDGEMENTS 11
CHAPTER 1. NEW AND SELECTIVE REACTIONS AND REAGENTS 12
REFERENCES 28
CHAPTER 2. APPLICATION OF SOME POLYMER SUPPORTED REAGENTS TO ORGANIC SYNTHESIS 30
REFERENCES 39
CHAPTER 3. MOLECULAR ENGINEERING: THE DESIGN AND SYNTHESIS OF CATALYSTS FOR THE RAPID 4-ELECTRON REDUCTION OF MOLECULAR OXYGEN TO WATER 40
REFERENCES 55
CHAPTER 4. SYNTHETIC APPLICATIONS OF THE CHEMISTRY OF DICARBONYL CYCLOPENTADIENYLIRON COMPLEXES 58
REFERENCES 65
CHAPTER 5. ZIRCONIUM REAGENTS IN ORGANIC SYNTHESIS 66
INTRODUCTION 66
GENERAL CONSIDERATIONS FOR TANDEM METAL SYNTHESIS SEQUENCES 66
REGIO-CONTROLLED COUPLING OF (p-ALLYLIC)PALLADIUM COMPLEXES WITH ORGANOZIRCONIUM SPECIES 66
NICKEL-CATALYZED CONJUGATE ADDITION REACTIONS 69
PREDICTION OF CARBON-CARBON COUPLING PROCESSES 71
CONCLUSIONS 72
REFERENCES 72
CHAPTER 6. ARENE–METAL COMPLEXES IN ORGANIC CHEMISTRY 
74 
INTRODUCTION 74
ADDITION TO h6-(STYRENE)CHROMIUM TRICARBONYL COMPLEXES 74
NEW SELECTIVITIES IN ADDITIONS TO SUBSTITUTED ARENE-Cr(CO)3 COMPLEXES 75
REFERENCES 80
CHAPTER 7. TRANSITION METAL MEDIATED CARBON-CARBON BOND FORMATIONS: A GENERAL, PARTIALLY CHEMO-, REGIO-, AND STEREOSPECIFIC SYNTHESIS OF ANNELATED CYCLOHEXADIENES FROM ACYCLIC STARTING MATERIALS 82
INTRODUCTION 82
INTRAMOLECULAR DIYNEENE CYCLIZATIONS 83
INTERMOLECULAR [2+2+2] CYCLIZATIONS 87
DECOMPLEXATIONS AND LIGAND REACTIONS 89
REACTIONS OF COMPLEXED DIENES 91
CONCLUSION 92
REFERENCES 92
CHAPTER 8. SOME USES OF SILICON COMPOUNDS IN ORGANIC SYNTHESIS 96
1. SILYL ENOL ETHERS 96
2. .-SILYL ALCOHOLS 99
REFERENCES 107
CHAPTER 9. NEW STRATEGIC METHODS FOR SYNTHESIS 108
TORGOV METHOD 108
XYLYLENE METHOD 109
GENERAL REITERATIVE REACTION 124
References 130
CHAPTER 10. THE RICH CHEMISTRY OF VINYLIC ORGANOBORANES 132
INTRODUCTION 132
HYDROBORATION OF ALKYNES WITH BORANE DERIVATIVES 134
DIRECTIVE EFFECTS 138
SYNTHESIS OF OTHER VINYLIC ORGANOBORANES 139
REPRESENTATIVE APPLICATIONS OF VINYLIC BORANES 140
CONCLUSION 147
REFERENCES 147
CHAPTER 11. SYNTHESIS OF POLYETHER ANTIBIOTICS. ADJACENT AND REMOTE ASYMMETRIC INDUCTION VIA CYCLIC HYDROBORATION 150
INTRODUCTION 150
DISCUSSION 151
CHAPTER 12. NEW METHODS FOR FORMATION OF CARBON–CARBON BONDS 
156 
INTRODUCTION 156
SYNTHESIS OF a-HALOENAMINES 157
a-HALOENAMINES AS ENOLATE EQUIVALENTS 158
KETENEIMINIUM SALTS AS ACYL CATION EQUIVALENTS 161
a-METALLED ENAMINES AS ACYL ANION EQUIVALENTS 165
a-CYANOENAMINES AS HOMOENOLATE EQUIVALENTS 168
a,ß DEHYDROGENATION OF CARBOXAMIDES 171
FINAL REMARKS 172
REFERENCES 172
CHAPTER 13. NEW REAGENTS BASED ON HETEROATOM- FACILITATED LITHIATIONS 174
REFERENCES 183
CHAPTER 14. SYNTHESIS AND REACTIONS OF NOVEL 3-OXO-l,2-DIAZETIDINIUM YLIDES 184
CHAPTER 15. SYNTHETIC STUDIES TOWARDS CALCIMYCIN 198
CALCIMYCIN 198
References 207
CHAPTER 16. MACROLIDE SYNTHESIS: 6-DESOXYERYTHRONOLIDE B VIA ALDOL CONDENSATIONS 208
BACKGROUND AND SYNTHETIC STRATEGIES 208
STEREOCHEMISTRY OF THE ALDOL REACTION 211
SYNTHESIS OF 6-DESOXYERYTHRONOLIDE 
220 
SYNTHESIS OF SECO-ACID AND LACTONIZATION 222
REFERENCES 225
CHAPTER 17. THE TOTAL SYNTHESIS OF QUADRONE 228
INTRODUCTION 228
RESULTS 230
References 240
CHAPTER 18. BIOMIMETIC PRENYLATION REACTIONS 
242 
INTRODUCTION 242
STRUCTURAL AND SYNTHETIC STUDIES IN THE BISABOLOL SERIES 245
BIOMIMETIC SYNTHESIS OF CHRYSANTHEMYL ALCOHOL 247
REFERENCES 250
CHAPTER 19. ASPECTS OF CARBOCYCLIC RING FORMATION AND MODIFICATION 
252 
INTRODUCTION 252
BIOMIMETIC MONOCYCLIZATION OF TERPENOIDS 252
MEDIUM AND LARGE RING FORMATION 255
CARBENOID REACTIONS AND CYCLOPENTENONE ANNULATION 258
REFERENCES AND NOTES 260
A TOTAL SYNTHESIS OF RACEMIG ERIOLANIN 262
REFERENCES AND FOOTNOTES 268
CHAPTER 20. TXA2 STRUCTURE. THE SYNTHESIS OF ALTERNATIVES 270
BIOLOGICAL ACTIVITIES 282
CHAPTER 21. NEW METHODOLOGIES RELATED TO PROSTAGLANDIN SYNTHESIS 284
References 295
CHAPTER 22. SYNTHETIC STUDIES IN THE ALKALOID FIELD 296
INTRODUCTION 296
AN UNUSUAL ALKYLATION OF AN ENAMINE 
297 
REACTION OP ALKOXYCARBONYL TRYPTAMINE WITH AN ESTER ALDEHYDE 298
ANOMALOUS NUCLEOPHILIC SUBSTITUTION AND OXIDATION 299
REACTION OP ACRYLIC ACID DERIVATIVES WITH ENAMINES 301
UTILIZATION OP THE UNWANTED EPIMER AND ENANTIOMER 303
ENMTIOSELECTIVE SYNTHESES 304
REFERENCES 308
CHAPTER 23. CHIRALLY SELECTIVE SYNTHESIS OF NATURAL PRODUCTS. THE 10-HYDROXY ANALOGS OF DIHYDROQUININE 310
CHAPTER 24. AN APPROACH TO THE SYNTHESIS OF HIGHER-CARBON SUGARS 318
INTRODUCTION 318
SYNTHESIS OF MONOSACCHARIDES FROM FURAN DERIVATIVES 319
SYNTHESIS OF 2-KETOSES 320
SYNTHESIS OF HIGHER-CARBON SUGARS FROM FURAN DERIVATIVES 321
FURAN DERIVATIVES 322
SYNTHESIS OF 8-DEOXYOCTOSES 326
ACKNOW LEDGEMENTS 
327 
REFERENCES 328
CHAPTER 25. CARBOHYDRATE DERIVATIVES IN THE ASYMMETRIC SYNTHESIS OF NATURAL PRODUCTS 330
ACKNOWLEDGEMENT 335
REFERENCES 336
CHAPTER 26. A PRACTICABLE SYNTHESIS OF THIENAMYCIN 338
REFERENCES 344
CHAPTER 27. APPROACHES TO THE SYNTHESIS OF TOPOLOGICALLY SPHERICAL MOLECULES. RECENT ADVANCES IN THE CHEMISTRY OF DODECAHEDRANE 346
ACCESSIBILITY OF CLOSED DILACTONE 346
PREPARATION OF OPEN DILACTONES AND THE COMPLICATIONS OF TRANSANNULAR REACTIVITY 347
UNUSUAL PHOTOISOMERIZATION OF A BRIDGED a-DIKETONE 
349 
TRISECO DERIVATIVES VIA DICHLORO DIESTER REDUCTION (AND METHYLATION) 
352 
THE MONOSECO LEVEL OF ELABORATION 355
INSTALLATION OF THE FINAL BOND 357
ACKNOWLEDGEMENTS 357
REFERENCES 358
INDEX 360

Produkt-Details

• Erscheint lt. Verlag: 31.1.2017
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• ISBN-10: 1-4831-5466-1 / 1483154661
• ISBN-13: 978-1-4831-5466-4 / 9781483154664