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.

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.

1;Front Cover;12;Stereoselective Synthesis (Part H);43;Copyright Page;54;Table of Contents ;105;FOREWORD;66;PREFACE;87;CONTRIBUTORS;128;PART 1: Stereoselective Synthesis;148.1;Chapter 1. Synthetic Routes to the Oxahydrindene Subunit of the Avermectin- Milbemycin Family of Antiparasitic Agents: A Review;168.1.1;1. Introduction: Isolation, Structure Elucidation, Biosynthesis, and Biological Activity of the Avermectins;168.1.2;2. Synthetic Routes to the Oxahydrindene Subunit of the Avermectins;228.1.3;Acknowledgments.;448.1.4;References;449;Chapter 2. A New Tandem Process and its Application to the Synthesis of Macrolide Antibiotics;489.1;1. Introduction;489.2;2. A new tandem process (Two-stage coupling process);489.3;3. Synthesis of the rifamycin S ansa-chain compound;509.4;4. Synthesis of the rifamycin W ansa-chain compound;529.5;5. Total synthesis of rifamycin W;599.6;6. Total synthesis of erythronolide A;619.7;7. Total synthesis of erythromycin A;669.8;8. Mechanistic considerations about the diastereoselective first step (Stage I) of the new tandem process;689.9;References;7210;Chapter 3. Stereoselective Synthetic and Mechanistic Chemistry of Bicyclomycin;7610.1;INTRODUCTION;7610.2;ISOLATION, STRUCTURAL ELUCIDATION AND BIOSYNTHESIS;7710.3;MECHANISM OF ACTION;10810.4;CONCLUDING REMARKS;12210.5;REFERENCES AND FOOTNOTES;12311;Chapter 4. The Role of Isocyanides in the Synthesis of ß-Lactam Antibiotics and Related Compounds;12611.1;1. INTRODUCTION;12611.2;2. ß-LACTAM ANTIBIOTICS;13111.3;3. MODIFICATIONS OF ß-LACTAM ANTIBIOTICS THROUGH ISOCYANIDE CHEMISTRY;14611.4;4. PERSPECTIVES;15111.5;REFERENCES;15312;Chapter 5. Synthesis of the lß-Methylcarbapenem Key Intermediates Yoshio Ito and Shiro Terashima;15812.1;1. Introduction;15812.2;2. Construction of the Carbapenem Framework;15912.3;3. Synthesis of Key lß-Methylcarbapenem Intermediates;16112.4;References;18813;Chapter 6. Chemical Studies of the Taxane Diterpenes Charles S. Swindell;19213.1;1. INTRODUCTION;19213.2;2. TOTAL SYNTHESIS;19413.3;3. THE DEVELOPMENT OF AN A-RING ANNULATION STRATEGY FOR TAXANE SYNTHESIS;21613.4;4. PARTIAL SYNTHESIS OF TAXOL AND ITS STRUCTURE-AOTVITY PROFILE;23013.5;5. BIOLOGICALLY ACTIVE TAXOL ANALOGUES WITH DELETED Á-RING SIDECHAIN SUBSTITUENTS AND VARIABLE C-2' CONFIGURATIONS;23413.6;ACKNOWLEDGMENT.;24013.7;REFERENCES;24014;Chapter 7. Recent Advances in the synthesis of Tumor-Promoting Diterpenes;24614.1;1. INTRODUCTION;24614.2;2. INGENANE SYNTHETIC STUDIES;24714.3;3. PHORBOL SYNTHETIC STUDIES;25814.4;REFERENCES;28515;Chapter 8. Hydroxylated Indolizidines and their Synthesis;28815.1;1. Introduction;28815.2;2. The 1-hydroxyindolizidines (octahydroindolizin-l-ols);29115.3;3. The 2-hydroxyindoIizidines (octahydroindolizin-2-ols);29615.4;4. The 5-hydroxy-4-oxyindolizidines;29715.5;5. The 6-hydroxyindolizidines (octahydroindo!izin-6-oIs);29815.6;6. The 7-hydroxyindoIizidines (octahydroindolizin-7-oIs);29915.7;7. Elaeokanine C;30215.8;8. The 8-hydroxyindoIizidines (octahydroindolizin-8-oIs);30615.9;9. The pumiliotoxins;30715.10;10. The allopumiliotoxins;31015.11;11. The 8a-hydroxyindoIizidines (octahydroindolizin-8a-oIs);31315.12;12. The 1,2-dihydroxyindoIizidines (octahydroindoIizin-l,2-dioIs);31615.13;13. Slaframine;31915.14;14. Swainsonine;32615.15;15. Swainsonine stereomers;33815.16;16. Castanospermine;34515.17;17. Castanospermine stereomers and analogues;35515.18;REFERENCES;36816;Chapter 9. A Survey of Indolo [2,3-a] carbazole Alkaloids and Related Natural Products;37816.1;1. INTRODUCTION;37816.2;2. OCCURRENCE;37816.3;3. BIOGENESIS;38616.4;4. SYNTHESIS;38816.5;5. BIOLOGICAL ACTIVITY;39716.6;6. CONCLUDING REMARKS;41216.7;ACKNOWLEDGEMENT;41516.8;REFERENCES;41517;Chapter 10. Synthetic Methodology for 2-Amino Alcohols of Biological Interest;42417.1;1. INTRODUCTION;42417.2;2. CHIRAL SYNTHONS FOR 2-AMINO ALCOHOLS;42917.3;3. CONVERSION PROCESSES TO 2-AMINO ALCOHOLS;43817.4;4. SYNT