Trost / Hutchinson Organic Synthesis Today and Tomorrow

Proceedings of the 3rd IUPAC Symposium on Organic Synthesis, Madison, Wisconsin, USA, 15-20 June 1980
1. Auflage 2017
ISBN: 978-1-4831-5466-4
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 364 Seiten, Web PDF

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.

Autoren/Hrsg.

Trost, Barry M.

Hutchinson, C. Richard

Inhaltsverzeichnis

1;Front Cover;1
2;Organic Synthesis Today and Tomorrow;4
3;Copyright;5
4;Table of Contents
;6
5;Organizing Committee;8
6;PREFACE;10
7;ACKNOWLEDGEMENTS;11
8;CHAPTER 1. NEW AND SELECTIVE REACTIONS AND REAGENTS;12
8.1;REFERENCES;28
9;CHAPTER 2. APPLICATION OF SOME POLYMER SUPPORTED REAGENTS TO ORGANIC SYNTHESIS;30
9.1;REFERENCES;39
10;CHAPTER 3. MOLECULAR ENGINEERING: THE DESIGN AND SYNTHESIS OF CATALYSTS FOR THE RAPID 4-ELECTRON REDUCTION OF MOLECULAR OXYGEN TO WATER;40
10.1;REFERENCES;55
11;CHAPTER 4. SYNTHETIC APPLICATIONS OF THE CHEMISTRY OF DICARBONYL CYCLOPENTADIENYLIRON COMPLEXES;58
11.1;REFERENCES;65
12;CHAPTER 5. ZIRCONIUM REAGENTS IN ORGANIC SYNTHESIS;66
12.1;INTRODUCTION;66
12.2;GENERAL CONSIDERATIONS FOR TANDEM METAL SYNTHESIS SEQUENCES;66
12.3;REGIO-CONTROLLED COUPLING OF (p-ALLYLIC)PALLADIUM COMPLEXES WITH ORGANOZIRCONIUM SPECIES;66
12.4;NICKEL-CATALYZED CONJUGATE ADDITION REACTIONS;69
12.5;PREDICTION OF CARBON-CARBON COUPLING PROCESSES;71
12.6;CONCLUSIONS;72
12.7;REFERENCES;72
13;CHAPTER 6. ARENE–METAL COMPLEXES IN ORGANIC CHEMISTRY
;74
13.1;INTRODUCTION;74
13.2;ADDITION TO h6-(STYRENE)CHROMIUM TRICARBONYL COMPLEXES;74
13.3;NEW SELECTIVITIES IN ADDITIONS TO SUBSTITUTED ARENE-Cr(CO)3 COMPLEXES;75
13.4;REFERENCES;80
14;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
14.1;INTRODUCTION;82
14.2;INTRAMOLECULAR DIYNEENE CYCLIZATIONS;83
14.3;INTERMOLECULAR [2+2+2] CYCLIZATIONS;87
14.4;DECOMPLEXATIONS AND LIGAND REACTIONS;89
14.5;REACTIONS OF COMPLEXED DIENES;91
14.6;CONCLUSION;92
14.7;REFERENCES;92
15;CHAPTER 8. SOME USES OF SILICON COMPOUNDS IN ORGANIC SYNTHESIS;96
15.1;1. SILYL ENOL ETHERS;96
15.2;2. .-SILYL ALCOHOLS;99
15.3;REFERENCES;107
16;CHAPTER 9. NEW STRATEGIC METHODS FOR SYNTHESIS;108
16.1;TORGOV METHOD;108
16.2;XYLYLENE METHOD;109
16.3;GENERAL REITERATIVE REACTION;124
16.4;References;130
17;CHAPTER 10. THE RICH CHEMISTRY OF VINYLIC ORGANOBORANES;132
17.1;INTRODUCTION;132
17.2;HYDROBORATION OF ALKYNES WITH BORANE DERIVATIVES;134
17.3;DIRECTIVE EFFECTS;138
17.4;SYNTHESIS OF OTHER VINYLIC ORGANOBORANES;139
17.5;REPRESENTATIVE APPLICATIONS OF VINYLIC BORANES;140
17.6;CONCLUSION;147
17.7;REFERENCES;147
18;CHAPTER 11. SYNTHESIS OF POLYETHER ANTIBIOTICS. ADJACENT AND REMOTE ASYMMETRIC INDUCTION VIA CYCLIC HYDROBORATION;150
18.1;INTRODUCTION;150
18.2;DISCUSSION;151
19;CHAPTER 12. NEW METHODS FOR FORMATION OF CARBON–CARBON BONDS
;156
19.1;INTRODUCTION;156
19.2;SYNTHESIS OF a-HALOENAMINES;157
19.3;a-HALOENAMINES AS ENOLATE EQUIVALENTS;158
19.4;KETENEIMINIUM SALTS AS ACYL CATION EQUIVALENTS;161
19.5;a-METALLED ENAMINES AS ACYL ANION EQUIVALENTS;165
19.6;a-CYANOENAMINES AS HOMOENOLATE EQUIVALENTS;168
19.7;a,ß DEHYDROGENATION OF CARBOXAMIDES;171
19.8;FINAL REMARKS;172
19.9;REFERENCES;172
20;CHAPTER 13. NEW REAGENTS BASED ON HETEROATOM- FACILITATED LITHIATIONS;174
20.1;REFERENCES;183
21;CHAPTER 14. SYNTHESIS AND REACTIONS OF NOVEL 3-OXO-l,2-DIAZETIDINIUM YLIDES;184
22;CHAPTER 15. SYNTHETIC STUDIES TOWARDS CALCIMYCIN;198
22.1;CALCIMYCIN;198
22.2;References;207
23;CHAPTER 16. MACROLIDE SYNTHESIS: 6-DESOXYERYTHRONOLIDE B VIA ALDOL CONDENSATIONS;208
23.1;BACKGROUND AND SYNTHETIC STRATEGIES;208
23.2;STEREOCHEMISTRY OF THE ALDOL REACTION;211
23.3;SYNTHESIS OF 6-DESOXYERYTHRONOLIDE
;220
23.4;SYNTHESIS OF SECO-ACID AND LACTONIZATION;222
23.5;REFERENCES;225
24;CHAPTER 17. THE TOTAL SYNTHESIS OF QUADRONE;228
24.1;INTRODUCTION;228
24.2;RESULTS;230
24.3;References;240
25;CHAPTER 18. BIOMIMETIC PRENYLATION REACTIONS
;242
25.1;INTRODUCTION;242
25.2;STRUCTURAL AND SYNTHETIC STUDIES IN THE BISABOLOL SERIES;245
25.3;BIOMIMETIC SYNTHESIS OF CHRYSANTHEMYL ALCOHOL;247
25.4;REFERENCES;250
26;CHAPTER 19. ASPECTS OF CARBOCYCLIC RING FORMATION AND MODIFICATION
;252
26.1;INTRODUCTION;252
26.2;BIOMIMETIC MONOCYCLIZATION OF TERPENOIDS;252
26.3;MEDIUM AND LARGE RING FORMATION;255
26.4;CARBENOID REACTIONS AND CYCLOPENTENONE ANNULATION;258
26.5;REFERENCES AND NOTES;260
26.6;A TOTAL SYNTHESIS OF RACEMIG ERIOLANIN;262
26.7;REFERENCES AND FOOTNOTES;268
27;CHAPTER 20. TXA2 STRUCTURE. THE SYNTHESIS OF ALTERNATIVES;270
27.1;BIOLOGICAL ACTIVITIES;282
28;CHAPTER 21. NEW METHODOLOGIES RELATED TO PROSTAGLANDIN SYNTHESIS;284
28.1;References;295
29;CHAPTER 22. SYNTHETIC STUDIES IN THE ALKALOID FIELD;296
29.1;INTRODUCTION;296
29.2;AN UNUSUAL ALKYLATION OF AN ENAMINE
;297
29.3;REACTION OP ALKOXYCARBONYL TRYPTAMINE WITH AN ESTER ALDEHYDE;298
29.4;ANOMALOUS NUCLEOPHILIC SUBSTITUTION AND OXIDATION;299
29.5;REACTION OP ACRYLIC ACID DERIVATIVES WITH ENAMINES;301
29.6;UTILIZATION OP THE UNWANTED EPIMER AND ENANTIOMER;303
29.7;ENMTIOSELECTIVE SYNTHESES;304
29.8;REFERENCES;308
30;CHAPTER 23. CHIRALLY SELECTIVE SYNTHESIS OF NATURAL PRODUCTS. THE 10-HYDROXY ANALOGS OF DIHYDROQUININE;310
31;CHAPTER 24. AN APPROACH TO THE SYNTHESIS OF HIGHER-CARBON SUGARS;318
31.1;INTRODUCTION;318
31.2;SYNTHESIS OF MONOSACCHARIDES FROM FURAN DERIVATIVES;319
31.3;SYNTHESIS OF 2-KETOSES;320
31.4;SYNTHESIS OF HIGHER-CARBON SUGARS FROM FURAN DERIVATIVES;321
31.5;FURAN DERIVATIVES;322
31.6;SYNTHESIS OF 8-DEOXYOCTOSES;326
31.7;ACKNOW LEDGEMENTS
;327
31.8;REFERENCES;328
32;CHAPTER 25. CARBOHYDRATE DERIVATIVES IN THE ASYMMETRIC SYNTHESIS OF NATURAL PRODUCTS;330
32.1;ACKNOWLEDGEMENT;335
32.2;REFERENCES;336
33;CHAPTER 26. A PRACTICABLE SYNTHESIS OF THIENAMYCIN;338
33.1;REFERENCES;344
34;CHAPTER 27. APPROACHES TO THE SYNTHESIS OF TOPOLOGICALLY SPHERICAL MOLECULES. RECENT ADVANCES IN THE CHEMISTRY OF DODECAHEDRANE;346
34.1;ACCESSIBILITY OF CLOSED DILACTONE;346
34.2;PREPARATION OF OPEN DILACTONES AND THE COMPLICATIONS OF TRANSANNULAR REACTIVITY;347
34.3;UNUSUAL PHOTOISOMERIZATION OF A BRIDGED a-DIKETONE
;349
34.4;TRISECO DERIVATIVES VIA DICHLORO DIESTER REDUCTION (AND METHYLATION)
;352
34.5;THE MONOSECO LEVEL OF ELABORATION;355
34.6;INSTALLATION OF THE FINAL BOND;357
34.7;ACKNOWLEDGEMENTS;357
34.8;REFERENCES;358
35;INDEX;360