Rahman Studies in Natural Products Chemistry

Stereoselective Synthesis (Part F)
1. Auflage 2013
ISBN: 978-1-4831-0097-5
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band Volume 10, 730 Seiten, Web PDF

Reihe: Studies in Natural Products Chemistry

Studies in Natural Products Chemistry, Volume 10: Stereoselective Synthesis (Part F) is a collection of articles about studies on important organic molecules. The book covers studies such as that on the synthesis of cembranes as well as its natural occurrence and bioactivity; the stereoselective synthesis of Vitamin D; the synthesis of isoquinolinequinone antibiotics; and the nucleophilic addition chemistry of polyunsaturated carbonyl compounds. Also covered in the book are subjects such as developments in the synthesis of medium ring ethers; the biological properties, chemistry, and synthesis of didemnins; and natural products synthesis based on novel ring transformation. The text is recommended for organic chemists who would like to know more about the progresses in the study of important organic molecules and their implications in different fields.

Autoren/Hrsg.

Rahman, Atta-Ur

Inhaltsverzeichnis

1;Front Cover;1
2;Stereoselective Synthesis (Part F)
;4
3;Copyright Page;5
4;Foreword;6
5;Preface;8
6;Table of Contents;10
7;Contributors;12
8;Chapter 1. Studies on the Synthesis of Cembranes;16
8.1;1. INTRODUCTION;16
8.2;2. NATURAL OCCURRENCE AND BIOACHVITY;17
8.3;3. SYNTHESIS;18
8.4;REFERENCES AND NOTES;53
9;Chapter 2. Stereoselective Synthesis of Vitamin D;56
9.1;1. INTRODUCTION;56
9.2;2. SYNTHESIS OF THE RING A SYSTEM;56
9.3;A. THE LYTHGOE PHOSPHINE OXIDE;56
9.4;B. LYTHGOE RING A ALDEHYDE;58
9.5;C. LYTHGOE ENYNE SYNTHON;59
9.6;D. CYCLOPROPANE RING A SYNTHON;61
9.7;3. C/D RING SYNTHESIS;62
9.8;A. LYTHGOE-INHOFFEN DIOL;62
9.9;B. MICHAEL ADDITION;64
9.10;C. INTRAMOLECULAR DIELS-ALDER REACTION;64
9.11;D. BICYCLOHEPTANE FRAGMENTATION;65
9.12;E. ALKYLATION;67
9.13;F. ALDOL;68
9.14;A. CONTROL OF CHIRALITY AT C-17, C-20;69
9.15;B. CONSTRUCTION OF . 22-23 UNSATURATION;76
9.16;C. INTRODUCTION OF THE 25-HYDROXY SIDE CHAIN;80
9.17;5. COUPLING OF RING A WITH THE C/D SYNTHON;81
9.18;A. WITTIG REACTION;81
9.19;C. VINYLALLENE APPROACH;83
9.20;6. CONCLUSIONS;85
9.21;7. REFERENCES;85
10;Chapter 3. Synthesis of Isoquinolinequinone Antibiotics;90
10.1;1. INTRODUCTION;90
10.2;2. SAFRAMYCINS;90
10.3;3. Naphthyridinomycins;116
10.4;4. Quinocarcins;128
10.5;REFERENCES;155
11;Chapter 4. Extended Conjugate Addition Reactions: The Synthesis and Nucleophilic Addition Chemistry of Polyunsaturated Carbonyl Compounds;160
11.1;1. INTRODUCTION;160
11.2;2. SYNTHETIC APPROACHES TO POLYUNSATURATED CARBONYL COMPOUNDS;167
11.3;3. EXTENDED CONJUGATE ADDITIONS TO POLYUNSATURATED CARBONYL COMPOUNDS;184
11.4;4. CONCLUSION;204
11.5;REFERENCES;205
12;Chapter 5. Recent Developments in the Synthesis of Medium Ring Ethers;214
12.1;1. INTRODUCTION;214
12.2;2. CYCLIZATION BY C-O BOND FORMATION;215
12.3;3. CYCLIZATION BY C-C BOND FORMATION;231
12.4;4. RING ENLARGEMENTS;245
12.5;5. CONCLUSIONS;249
12.6;REFERENCES;250
13;Chapter 6. The Didemnins: Biological Properties, Chemistry and Total Synthesis;254
13.1;1. INTRODUCTION;254
13.2;2. BIOLOGICAL PROPERTIES OF THE DIDEMNINS;266
13.3;3. STRUCTURAL INVESTIGATIONS AND CONFORMATIONAL STUDIES OF DIDEMNINS A AND B;271
13.4;4. SYNTHETIC STUDIES;284
13.5;5. CONCLUSIONS;311
13.6;ACKNOWLEDGMENTS;312
13.7;REFERENCES;312
14;Chapter 7. Natural Products Synthesis based on Novel Ring Transformation;316
14.1;1. INTRODUCTION;316
14.2;2. RING TRANSFORMATION OF FIVE- AND SK-MEMBERED RINGS;317
14.3;3. CONSTRUCTION OF SEVEN-MEMBERED RINGS BASED ON RING TRANSFORMATION;322
14.4;4. CONVERSION OF MONOCYCLIC KETONES TO BICYCLIC ENONES;324
14.5;5. CONSTRUCTION OF SPIROCYCLIC SKELETONS;326
14.6;6. TRANSFORMATION OF BICYCLO[3.3.0]OCTANONES TO BICYCLO[3.2.1]OCTENES;330
14.7;7. RING CLEAVAGE BASED ON INTERMOLECULAR ALDOL CONDENSATION;331
14.8;8. SYNTHESIS OF (-)-PHORACANTHOLIDE I BASED ON STEREOSPECIFIC FRAGMENTATION REACTIONS;333
14.9;9. AN INSIGHT INTO THE NOVEL RING TRANSFORMATION;337
14.10;10. A BASE-CATALYZED FACILE RING ENLARGEMENT;340
14.11;REFERENCES AND NOTES;346
15;Chapter 8. Recent Developments in C-Glycoside Synthesis;350
15.1;1. INTRODUCTION;350
15.2;2. UNSATURATED SUGARS;350
15.3;3. GLYCOSIDES;368
15.4;4. LACTONES;398
15.5;REFERENCES;408
16;Chapter 9. Natural Product Synthesis Starting with Carbohydrates based on the Claisen Rearrangement Protocol;418
16.1;1. Introduction;418
16.2;2. The Johnson-Claisen Rearrangements of Allylic Alcohols Prepared from D-Glucose and their Stereoselectivity Considerations;441
16.3;3. Natural Product Synthesis Starting from the Claisen Rearrangement Products;452
16.4;Acknowledgment;461
16.5;References;461
17;Chapter 10. The Synthesis of Blood Group I and i Active Oligosaccharides;470
17.1;1. INTRODUCTION;470
17.2;2. STRUCTURAL STUDIES;470
17.3;3. SYNTHESES OF LACTOSAMINE (TYPE 2 CHAIN) AND DERIVATIVES;474
17.4;4. SYNTHESES OF LACTO-N-BIOSE I (TYPE 1 CHAIN) AND DERIVATIVES;480
17.5;5. ENZYMATIC SYNTHESES OF LACTOSAMINE AND LACTO-N-BIOSE I;481
17.6;6. CHEMICAL ACTIVATION OF GLUCOSAMINE, LACTOSAMINE, AND LACTO-N-BIOSE I;485
17.7;7. CHEMICAL SYNTHESES OF I- AND i-ACTIVE OLIGOSACCHARIDES;487
17.8;8. ENZYMATIC SYNTHESES OF I- AND i-ACTIVE OLIGOSACCHARIDES;492
17.9;9. SYNTHETIC OLIGOSACCHARIDES AS TOOLS IN BIOLOGICAL STUDIES OF Ii SUBSTANCES;493
17.10;REFERENCES;499
18;Chapter 11. Glycosidase and Glycosyltransferase Inhibitors;508
18.1;1. INTRODUCTION;508
18.2;2. GLYCOSIDASE AND GLYCOSYLTRANSFERASE;509
18.3;3. INHIBITORS;516
18.4;ACKNOWLEDGEMENTS;587
18.5;REFERENCES;587
19;Chapter 12. Synthesis of Oxetanocin, Novel Nucleoside Containing an Oxetane Ring and its Carbocyclic Analogues;598
19.1;1. INTRODUCTION;598
19.2;2. TRANSFORMATION OF OXETANOCIN A TO OTHER OXETANOCINS;599
19.3;3. TOTAL SYNTHESIS OF OXETANOCIN A;600
19.4;4. SYNTHESIS OF CARBOCYCLIC OXETANOCINS;621
19.5;5. ANTIVIRAL ACTIVITY;632
20;Chapter 13. Biomimetic Synthesis of Macrocyclic Oligopeptides having Isodityrosine and Related Units;642
20.1;1. Introduction;642
20.2;2. SYNTHETIC METHOD;642
20.3;3. BASTADINS;645
20.4;4. PIPERAZINOMYCIN;651
20.5;5. BOUVARDINS;653
20.6;6. ANTIBIOTIC OF 4949-III AND RELATED SUBSTANCES;659
20.7;7. ANTIBIOTIC K-13;665
20.8;8. VANCOMYCIN AND RELATED ANTIBIOTICS;670
20.9;9. CONCLUSION;680
20.10;References;680
21;Chapter 14. Asymmetric Synthesis of Chiral Alkaloids using Chiral Sulfur Reagents;684
21.1;1. INTRODUCTION;684
21.2;2. INTRAMOLECULAR ADDITION OF AMINE NUCLEOPHILES TO CHIRAL VINYL SULFOXIDES AND SULFOXIMINES;684
21.3;3. ADDITION OF THE ANIONS OF CHIRAL SULFOXIDES AND SULFOXIMINES TO 3,4-DIHYDRO-6,7-DIMETHOXYISOQUINOLINE;692
21.4;4. DIASTEREOSELECTIVE REDUCTION OF ß-SULFINYL ENAMIDES AND ENAMINES;701
21.5;5. CONCLUSION;701
21.6;REFERENCES;702
22;Subject Index;704