Knolker The Alkaloids

1. Auflage 2015
ISBN: 978-0-12-802356-3
Verlag: Elsevier Science & Techn.
Format: EPUB
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, Band Volume 74, 438 Seiten

Reihe: The Alkaloids

For more than 60 years, The Alkaloids has been the leading book series in the field of alkaloid chemistry. In more than 70 volumes all aspects of alkaloids, including chemistry, biology and pharmacology, have been covered in high-quality timeless reviews written by renowned experts in the field. - The Alkaloids is the leading book series in the field of alkaloid chemistry - In more than 70 volumes all aspects of alkaloids, including chemistry, biology and pharmacology, have been covered

Autoren/Hrsg.

Knolker, Hans-Joachim

Inhaltsverzeichnis

1;Front Cover;1
2;The Alkaloids Chemistry and Biology;2
3;The Alkaloids Chemistry and BiologyEdited byHans-Joachim KnölkerDepartment Chemie Technische Universität Dresden Dresden Ge ...;4
4;Copyrights
;5
5;Contents;6
6;Contributors;8
7;Preface;10
8;The Securinega Alkaloids;12
8.1;1. Introduction;16
8.2;2. Occurrence;18
8.3;3. Securinine-type Alkaloids;19
8.3.1;3.1 Securinine (1)/Virosecurinine (2), Allosecurinine (3) (Phyllochrysine)/Viroallosecurinine (4);19
8.3.1.1;3.1.1 NMR Spectrum Analysis of Securinine;29
8.3.1.2;3.1.2 Conformational Study on Securinega Alkaloids;33
8.3.1.3;3.1.3 X-Ray Crystal Structure of Securinine/Virosecurinine Free Base;35
8.3.2;3.2 14,15-Dihydrosecurinine (5);35
8.3.3;3.3 Phyllanthidine (6), Ent-Phyllanthidine (7);36
8.3.4;3.4 Secu'amamine D (8);38
8.3.5;3.5 Margaritarine (9);39
8.3.6;3.6 Secu'amamine B (10);40
8.3.7;3.7 Secu'amamine C (11);40
8.3.8;3.8 15a-Methoxy-14,15-Dihydrophyllochrysine (12);41
8.3.9;3.9 15-a-Hydroxy-14,15-dihydroallosecurinine/Securinol C (13);41
8.3.10;3.10 4a-Hydroxy-15a-Methoxy-14,15-Dihydroallosecurinine (14);42
8.3.11;3.11 4a,15a-Dimethoxy-14,15-Dihydrosecurinine (15);43
8.3.12;3.12 4a-Hydroxyallosecurinine (16);44
8.3.13;3.13 Phyllanthine (17);44
8.3.14;3.14 4-Epiphyllanthine (18);45
8.3.15;3.15 Securitinine (19);46
8.3.16;3.16 Flueggedine (20);46
8.4;4. Neosecurinane Alkaloids;48
8.4.1;4.1 Securinol A (21) and Virosine A (Securinol B) (22);48
8.4.2;4.2 Virosine B (23);49
8.4.3;4.3 Secu'amamine E (24);50
8.4.4;4.4 Secu'amamine F and G (25 and 26);51
8.5;5. Norsecurinine-type Alkaloids;51
8.5.1;5.1 Norsecurinine (27);51
8.5.2;5.2 14,15-Dihydronorsecurinine (Virosine) (28);52
8.5.3;5.3 14,15-Epoxynorsecurinine (29);52
8.5.4;5.4 Simplexine (30);53
8.5.5;5.5 4-Methoxynorsecurinine (31);54
8.5.6;5.6 Flueggeainol (32) and Fluggeainol Ether (33);54
8.5.7;5.7 15ß-Hydroxy-14,15-Dihydronorsecurinine (34);55
8.5.8;5.8 15ß-Methoxy-14,15-Dihydronorsecurinine (35);55
8.5.9;5.9 15a-Methoxy-14,15-Dihydronorsecurinine (36);56
8.5.10;5.10 Secu'amamine A (37);56
8.5.11;5.11 Virosaines A (38) and B (39);57
8.6;6. Neonorsecurinane Alkaloids;58
8.6.1;6.1 Bubbialine (40);59
8.6.2;6.2 Bubbialidine (41);60
8.6.3;6.3 Isobubbialine (42);60
8.6.4;6.4 Epibubbialine (43);61
8.6.5;6.5 Niruroidine (44);61
8.6.6;6.6 Nirurine (45);62
8.7;7. Norsecurinine-Derived Oligomeric Alkaloids;63
8.7.1;7.1 Flueggine A (46);63
8.7.2;7.2 Flueggine B (47);64
8.7.3;7.3 Flueggenine A (48);65
8.7.4;7.4 Flueggenine B (49);66
8.7.5;7.5 Flueggenine C (50);67
8.7.6;7.6 Flueggenine D (51);67
8.7.7;7.7 Fluevirosine A (52);68
8.7.8;7.8 Fluevirosine B (53);69
8.7.9;7.9 Fluevirosine C (54);70
8.7.10;7.10 Fluevirosine D (55);70
8.7.11;7.11 Fluevirosinine A (56);71
8.8;8. Synthesis;72
8.8.1;8.1 Synthesis of Securinine (1) and its Stereoisomers (2–4);72
8.8.1.1;8.1.1 Horii Synthesis;73
8.8.1.2;8.1.2 Honda Synthesis of Compound 82;73
8.8.1.3;8.1.3 Liras Synthesis;75
8.8.1.4;8.1.4 Honda Synthesis;75
8.8.1.5;8.1.5 Kerr Synthesis;78
8.8.1.6;8.1.6 Busqué and de March Synthesis;79
8.8.1.7;8.1.7 Thadani Synthesis;81
8.8.1.8;8.1.8 Alibès and de March Synthesis;82
8.8.1.9;8.1.9 Wood Synthesis;83
8.8.1.10;8.1.10 Bayón and Figueredo Synthesis;85
8.8.2;8.2 Synthesis of Norsecurinine (27);86
8.8.2.1;8.2.1 Heathcock Synthesis;87
8.8.2.2;8.2.2 Jacobi Synthesis;89
8.8.2.3;8.2.3 Magnus Synthesis;89
8.8.2.4;8.2.4 Weinreb Synthesis;92
8.8.2.5;8.2.5 Bayón and Figueredo Synthesis;93
8.8.2.6;8.2.6 Yang and Li Synthesis;94
8.8.3;8.3 Synthesis of 14,15-Dihydronorsecurinine (28);94
8.8.4;8.4 Synthesis of Nirurine (45);95
8.8.5;8.5 Synthesis of Phyllanthine (17);96
8.8.6;8.6 Synthesis of Ent-Phyllanthidine (7);97
8.8.7;8.7 Synthesis of Secu'amamine A (37);99
8.8.8;8.8 Synthesis of 3-Deshydroxy-secu'amamine A (222);100
8.8.9;8.9 Synthesis of Flueggine A (46);103
8.8.10;8.10 Synthesis of Virosaine B (39);104
8.8.11;8.11 Synthesis of Bubbialidine (41) and Virosaine A (38);105
8.8.12;8.12 Synthesis of Allonorsecurinine (254);107
8.9;9. Biosynthesis;108
8.9.1;9.1 General Pathway;108
8.9.2;9.2 Biosynthesis of Nirurine (45);111
8.9.3;9.3 Biosynthesis of Secu'amamine A (37);112
8.9.4;9.4 Biosynthesis of Virosaines A (38) and B (39);113
8.9.5;9.5 Biosynthesis of Norsecurinine-Based Oligomers;115
8.9.6;9.6 Biosynthesis of Flueggedine (20);117
8.10;10. Biological Activities—Pharmacological Activities;118
8.10.1;10.1 Central Nervous System Properties;119
8.10.2;10.2 Oncologic Properties;121
8.10.3;10.3 Antimicrobial Properties;124
8.11;11. Summary and Conclusions;125
8.12;Acknowledgments;126
8.13;References;127
9;The Homalium Alkaloids: Isolation, Synthesis, and Absolute Configuration Assignment;132
9.1;1. Introduction;133
9.1.1;1.1 Isolation;133
9.1.2;1.2 Structure Elucidation;134
9.2;2. Homaline and Hopromine;135
9.2.1;2.1 Syntheses of Homaline and Hopromine;135
9.2.2;2.2 Spectroscopic Data for Homaline and Hopromine;147
9.3;3. Hoprominol and Hopromalinol;147
9.3.1;3.1 Syntheses of Hoprominol and Hopromalinol;147
9.3.2;3.2 Spectroscopic Data for Hoprominol and Hopromalinol;162
9.4;4. Conclusion;162
9.5;References;169
10;The Alkaloids of the Madangamine Group;170
10.1;1. Introduction;171
10.2;2. Isolation and Characterization;173
10.2.1;2.1 Isolation;173
10.2.2;2.2 Physical and Spectral Properties;177
10.3;3. Biogenesis;187
10.4;4. Biological Activity;190
10.5;5. Synthesis;191
10.5.1;5.1 Construction of the Diazatricyclic ABC Core;191
10.5.1.1;5.1.1 Weinreb's Approach;191
10.5.1.2;5.1.2 Kibayashi's Approach;192
10.5.1.3;5.1.3 Marazano's Biomimetic Approach;194
10.5.1.4;5.1.4 Bonjoch's Approach;196
10.5.1.5;5.1.5 The Amat–Bosch Enantioselective Approach;197
10.5.2;5.2 Closure of the Western D Ring;201
10.5.2.1;5.2.1 Model Studies;201
10.5.2.2;5.2.2 From Functionalized Diazatricyclic Intermediates;202
10.5.3;5.3 Closure of the Eastern E Ring;204
10.5.3.1;5.3.1 Model Studies;204
10.5.3.2;5.3.2 From Functionalized Diazatricyclic Intermediates;206
10.5.4;5.4 First Total Synthesis of (+)-Madangamine D;206
10.6;6. Summary;208
10.7;Acknowledgments;209
10.8;References;209
11;The Veratrum and Solanum Alkaloids;212
11.1;1. Introduction;212
11.2;2. Structures of Veratrum and Solanum Alkaloids;215
11.2.1;2.1 The Jervanine Subgroup;215
11.2.2;2.2 The Veratramine Subgroup;216
11.2.3;2.3 The Cevanine Subgroup;216
11.2.4;2.4 The Solanidine Subgroup;223
11.2.5;2.5 The Verazine Subgroup;225
11.3;3. Chemistry of Veratrum and Solanum Alkaloids;227
11.4;4. Biological and Medicinal Properties of Veratrum and Solanum Alkaloids;234
11.5;5. Summary;236
11.6;Acknowledgments;237
11.7;References;237
12;Alkaloids of the Annonaceae: Occurrence and a Compilation of Their Biological Activities;244
12.1;1. Introduction;245
12.2;2. Botanical Features of the Annonaceae;246
12.2.1;2.1 Distribution and Origin;246
12.2.2;2.2 Diagnostic Features;247
12.2.3;2.3 Classification;247
12.3;3. Alkaloids of the Annonaceae;248
12.4;4. Organization of the Data;258
12.5;5. Classification of the Alkaloids of the Annonaceae;258
12.5.1;5.1 Simple Isoquinolines, Isoquinolones, and Phenethylammonium (Type I);258
12.5.2;5.2 Benzyltetrahydroisoquinolines, Seco-Benzylisoquinolines, and Benzylisoquinolines (Type II);338
12.5.3;5.3 Bisbenzylisoquinolines (Type III) and Bisbenzyltetrahydroisoquinolines (Type IV);338
12.5.4;5.4 Protoberberines (Type V) and Tetrahydroprotoberberines (Type VI);338
12.5.5;5.5 Proaporphines (Type VII);339
12.5.6;5.6 Aporphinoids (Type VIII), Dehydroaporphines (Type IX), and 4- or 7-Substituted Aporphines (Type X);339
12.5.7;5.7 Oxoaporphines (Type XI);340
12.5.8;5.8 Phenanthrenes (Type XII);340
12.5.9;5.9 Miscellaneous Isoquinoline-Type Alkaloids (Type XIII);341
12.5.10;5.10 Nonisoquinoline Alkaloids (Type XIV);341
12.6;6. Conclusions;342
12.7;References;406
13;Cumulative Index of Titles;422
14;Index;434