Rahman Studies in Natural Products Chemistry

Stereoselective Synthesis
1. Auflage 2013
ISBN: 978-1-4831-9324-3
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band Volume 12, 548 Seiten, Web PDF

Reihe: Studies in Natural Products Chemistry

Studies in Natural Products Chemistry Volume 12: Stereoselective Synthesis (Part H) reviews the stereoselective synthetic and mechanistic chemistry of bicyclomycin. It discusses chemical studies of the taxane diterpenes; the synthetic methodology for 2-amino alcohols of biological interest; and the synthesis and structure of hydroxylated indolizidines. Some of the topics covered in the book are the synthetic routes to the oxahydrindene subunit of the avermectin-milbemycin family of antiparasitic agents; isolation, structure elucidation, biosynthesis, and biological activity of the avermectins; two-stage coupling process of macrolide antibiotics synthesis; and synthesis of the rifamycin S ansa-chain compound. The complete synthesis of erythromycin A is also covered. The role of isocyanides in the synthesis of beta lactam antibiotics and the characteristics of the beta lactam antibiotics are discussed. The development of an A-Ring annulation strategy for taxane synthesis is also presented. A chapter is devoted to the advances in the synthesis of tumor-promoting diterpenes. The book can provide useful information to chemists, biologists, students, and researchers.

Autoren/Hrsg.

Rahman, Atta-Ur

Inhaltsverzeichnis

1;Front Cover;1
2;Stereoselective Synthesis (Part H);4
3;Copyright Page;5
4;Table of Contents ;10
5;FOREWORD;6
6;PREFACE;8
7;CONTRIBUTORS;12
8;PART 1: Stereoselective Synthesis;14
8.1;Chapter 1. Synthetic Routes to the Oxahydrindene Subunit of the Avermectin- Milbemycin Family of Antiparasitic Agents: A Review;16
8.1.1;1. Introduction: Isolation, Structure Elucidation, Biosynthesis, and Biological Activity of the Avermectins;16
8.1.2;2. Synthetic Routes to the Oxahydrindene Subunit of the Avermectins;22
8.1.3;Acknowledgments.;44
8.1.4;References;44
9;Chapter 2. A New Tandem Process and its Application to the Synthesis of Macrolide Antibiotics;48
9.1;1. Introduction;48
9.2;2. A new tandem process (Two-stage coupling process);48
9.3;3. Synthesis of the rifamycin S ansa-chain compound;50
9.4;4. Synthesis of the rifamycin W ansa-chain compound;52
9.5;5. Total synthesis of rifamycin W;59
9.6;6. Total synthesis of erythronolide A;61
9.7;7. Total synthesis of erythromycin A;66
9.8;8. Mechanistic considerations about the diastereoselective first step (Stage I) of the new tandem process;68
9.9;References;72
10;Chapter 3. Stereoselective Synthetic and Mechanistic Chemistry of Bicyclomycin;76
10.1;INTRODUCTION;76
10.2;ISOLATION, STRUCTURAL ELUCIDATION AND BIOSYNTHESIS;77
10.3;MECHANISM OF ACTION;108
10.4;CONCLUDING REMARKS;122
10.5;REFERENCES AND FOOTNOTES;123
11;Chapter 4. The Role of Isocyanides in the Synthesis of ß-Lactam Antibiotics and Related Compounds;126
11.1;1. INTRODUCTION;126
11.2;2. ß-LACTAM ANTIBIOTICS;131
11.3;3. MODIFICATIONS OF ß-LACTAM ANTIBIOTICS THROUGH ISOCYANIDE CHEMISTRY;146
11.4;4. PERSPECTIVES;151
11.5;REFERENCES;153
12;Chapter 5. Synthesis of the lß-Methylcarbapenem Key Intermediates Yoshio Ito and Shiro Terashima;158
12.1;1. Introduction;158
12.2;2. Construction of the Carbapenem Framework;159
12.3;3. Synthesis of Key lß-Methylcarbapenem Intermediates;161
12.4;References;188
13;Chapter 6. Chemical Studies of the Taxane Diterpenes Charles S. Swindell;192
13.1;1. INTRODUCTION;192
13.2;2. TOTAL SYNTHESIS;194
13.3;3. THE DEVELOPMENT OF AN A-RING ANNULATION STRATEGY FOR TAXANE SYNTHESIS;216
13.4;4. PARTIAL SYNTHESIS OF TAXOL AND ITS STRUCTURE-AOTVITY PROFILE;230
13.5;5. BIOLOGICALLY ACTIVE TAXOL ANALOGUES WITH DELETED Á-RING SIDECHAIN SUBSTITUENTS AND VARIABLE C-2' CONFIGURATIONS;234
13.6;ACKNOWLEDGMENT.;240
13.7;REFERENCES;240
14;Chapter 7. Recent Advances in the synthesis of Tumor-Promoting Diterpenes;246
14.1;1. INTRODUCTION;246
14.2;2. INGENANE SYNTHETIC STUDIES;247
14.3;3. PHORBOL SYNTHETIC STUDIES;258
14.4;REFERENCES;285
15;Chapter 8. Hydroxylated Indolizidines and their Synthesis;288
15.1;1. Introduction;288
15.2;2. The 1-hydroxyindolizidines (octahydroindolizin-l-ols);291
15.3;3. The 2-hydroxyindoIizidines (octahydroindolizin-2-ols);296
15.4;4. The 5-hydroxy-4-oxyindolizidines;297
15.5;5. The 6-hydroxyindolizidines (octahydroindo!izin-6-oIs);298
15.6;6. The 7-hydroxyindoIizidines (octahydroindolizin-7-oIs);299
15.7;7. Elaeokanine C;302
15.8;8. The 8-hydroxyindoIizidines (octahydroindolizin-8-oIs);306
15.9;9. The pumiliotoxins;307
15.10;10. The allopumiliotoxins;310
15.11;11. The 8a-hydroxyindoIizidines (octahydroindolizin-8a-oIs);313
15.12;12. The 1,2-dihydroxyindoIizidines (octahydroindoIizin-l,2-dioIs);316
15.13;13. Slaframine;319
15.14;14. Swainsonine;326
15.15;15. Swainsonine stereomers;338
15.16;16. Castanospermine;345
15.17;17. Castanospermine stereomers and analogues;355
15.18;REFERENCES;368
16;Chapter 9. A Survey of Indolo [2,3-a] carbazole Alkaloids and Related Natural Products;378
16.1;1. INTRODUCTION;378
16.2;2. OCCURRENCE;378
16.3;3. BIOGENESIS;386
16.4;4. SYNTHESIS;388
16.5;5. BIOLOGICAL ACTIVITY;397
16.6;6. CONCLUDING REMARKS;412
16.7;ACKNOWLEDGEMENT;415
16.8;REFERENCES;415
17;Chapter 10. Synthetic Methodology for 2-Amino Alcohols of Biological Interest;424
17.1;1. INTRODUCTION;424
17.2;2. CHIRAL SYNTHONS FOR 2-AMINO ALCOHOLS;429
17.3;3. CONVERSION PROCESSES TO 2-AMINO ALCOHOLS;438
17.4;4. SYNTHETIC APPLICATIONS TO HYDROXY AMINO ACIDS;444
17.5;5. Conclusion;451
17.6;References and Notes;452
18;Chapter 11. Stereoselective Synthesis of Natural Products via Cationicand Radical Intermediates;458
18.1;1. INTRODUCTION;458
18.2;2. INTRAMOLECULAR ARYLATION OF N-ACYLIMINIUM IONS;460
18.3;3. N-ACYLIMINIUM ION-VINYLSILANE CYCLIZATION IN THE SYNTHESIS OF;466
18.4;4. N-ACYCLIM1NIUM ION INITIATED POLYENE CYCLIZATION;469
18.5;5. á-ACYLAMINO RADICAL CYCLIZATION IN A SYNTHESIS OF PYRROLIDINE AND PIPERIDINE DERIVATIVES;484
18.6;6. STEREOSELECTIVE SYNTHESIS OF ß-OXYGENATED .-AMINO ACIDS;489
18.7;REFERENCES;506
19;SUBJECT INDEX;512