Syntheses of the benzo-c-phenanthridine alkaloids
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| Format: | Buch |
| Sprache: | English |
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Budapest
Akad. Kiadó
1984
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| Schriftenreihe: | Recent developments in the chemistry of natural carbon compounds
10 |
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| 100 | 1 | |a Ninomiya, I. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Syntheses of the benzo-c-phenanthridine alkaloids |c by I. Ninomiya and T. Naito |
| 264 | 1 | |a Budapest |b Akad. Kiadó |c 1984 | |
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| 336 | |b txt |2 rdacontent | ||
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| 490 | 1 | |a Recent developments in the chemistry of natural carbon compounds |v 10 | |
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Benzophenanthridinalkaloide |0 (DE-588)4334860-9 |2 gnd |9 rswk-swf |
| 655 | 7 | |a Vancomycin-Antibiotika |2 gnd |9 rswk-swf | |
| 689 | 0 | 0 | |a Vancomycin-Antibiotika |A f |
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| 689 | 1 | 0 | |a Benzophenanthridinalkaloide |0 (DE-588)4334860-9 |D s |
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| 700 | 1 | |a Naito, T. |e Verfasser |4 aut | |
| 700 | 1 | 2 | |a Sztaricskai, F. |4 aut |t The chemistry of the vancomycin group of antibiotics |
| 700 | 1 | 2 | |a Bognár, R. |4 aut |t The chemistry of the vancomycin group of antibiotics |
| 830 | 0 | |a Recent developments in the chemistry of natural carbon compounds |v 10 |w (DE-604)BV006654905 |9 10 | |
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| 249 | |a <<The>> chemistry of the vancomycin group of antibiotics |v by F. Sztaricskai and R. Bognár | ||
Datensatz im Suchindex
| _version_ | 1804120942013579264 |
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| adam_text | 4. SYNTHESES OF THE BENZO[C]PHENANTHRIDINE ALKALOIDS BY I. NINOMIYA T.
NAITO ^ KOBE WOMEN S COLLEGE OF PHARMACY MOTOYAMAKILA, HIGASHINADA, KOBE
658, JAPAN THE CHEMISTRY OF THE VANCOMYCIN GROUP OF ANTIBIOTICS BY F.
SZTARICSKAI * R. BOGNAR Y RESEARCH GROUP FOR ANTIBIOTICS OF THE
HUNGARIAN ACADEMY OF SCIENCES * AND INSTITUTE OF ORGANIC CHEMISTRY
KOSSUTH LAJOS UNIVERSITY, DEBRECEN. HUNGARY -1828- UNIVERSITATS-
BIBLIOTHEK AK.ADEMIAI KIADO PUBLISHING HOUSE OF THE HUNGARIAN ACADEMY OF
SCIENCES BUDAPEST 1984 CONTENTS I. NINOMIYA AND T. NAITO SYNTHESES OF
THE BENZOFCJPHENANTHRIDINE ALKALOIDS 1. INTRODUCTION 11 1.1.
CLASSIFICATION OF BENZO[C]PHENANTHRIDINE ALKALOIDS 11 1.1.1. FULLY
AROMATIC AND RELATED ALKALOIDS 13 1.1.2.
B/C-HEXAHYDROBENZO[C]PHENANTHRIDINE ALKALOIDS 14 1.1.3. DERIVED
ANALOGUES OF BENZO[C]PHENANTHRIDINE ALKALOIDS 16 1.2. BIOSYNTHESIS OF
BENZO[C]PHENANTHRIDINE ALKALOIDS 16 2. THE CHEMISTRY OF INDIVIDUAL
BENZO[C]PHENANTHRIDINE ALKALOIDS 20 2.1. THE CHEMISTRY OF THE FULLY
AROMATIC ALKALOIDS 20 2.2. THE CHEMISTRY OF THE
B/C-HEXAHYDROBENZO[C]PHENANTHRIDINE ALKALOIDS 23 2.2.1. THE CHEMISTRY OF
THE CHELIDONINE ALKALOIDS 23 2.2.2, THE CHEMISTRY OF THE CORYNOLINE
ALKALOIDS 27 3. SYNTHETIC METHODOLOGY FOR BENZO[C]PHENANTHRIDINE
ALKALOIDS 30 3.1. SYNTHETIC METHODS INVOLVING THE FORMATION OF RING B AS
THE FINAL STEP IN THE CONSTRUCTION OF THE BENZO[C]PHENANTHRIDINE
SKELETON 32 3.1.1. THE APPLICATION OF THE BISCHLER-NAPIERALSKI
CYCLIZATION 32 3.1.2. SYNTHESIS VIA THE CYCLIZATION OF A BENZYNE
INTERMEDIATE .-.. 36 3.1.3. ENAMIDE PHOTOCYCLIZATION FOR THE SYNTHESIS
OF BENZO[C]PHENANTHRIDINES :. 38 3.2. SYNTHESIS VIA THE FORMATION OF
RING C AS THE FINAL STEP 42 3.2.1. PHOTOCYCLIZATION OF STILBENE TYPE
TRIENES :.... 42 3.2.2. PHOTOCYCLIZATION OF TRIENES FORMED IN THE
HOFMANN DEGRADATION OF PROTOBERBERINE ALKALOIDS 44 3.2.3. PSCHORR
CYCLIZATION LEADING TO BENZO[C]PHENANTHRIDINES 48 3.2.4. SYNTHESIS OF
BENZO[C]PHENANTHRIDINES VIA ISOCARBOSTYRILS 48 3.2.5. SYNTHESIS OF
BENZO[C]PHENANTHRIDINES VIA THE CONDENSATION OF HOMOPHTHALATE WITH A
SCHIFF BASE 51 3.3. ANOTHER APPROACH FOR THE SYNTHESIS OF
BENZO[C]PHENANTHRIDINES 54 3.3.1. INTRAMOLECULAR CYCLOADDITION OF
O-QUINODIMETHANES TO ACETYLENES 54 4. TOTAL SYNTHESIS OF
BENZO[C]PHENANTHRIDINE ALKALOIDS 56 4.1. TOTAL SYNTHESIS OF THE FULLY
AROMATIC ALKALOIDS 56 4.1.1. SYNTHESIS OF THE 2,3,7,8-TETRASUBSTITUTED
ALKALOIDS 56 6 CONTENTS 4.1.1.1. SYNTHESIS OF CHELERYTHRINE VIA
CYCLIZATION OF A HOMOPHTHALIC ANHYDRIDE 57 4.1.1.2. SYNTHESIS OF
CHELERYTHRINE VIA BENZYNE CYCLIZATION 58 4.1.1.3. SYNTHESIS OF
CHELERYTHRINE VIA ENAMIDE PHOTOCYCLIZATION 58 4.1.1.4. CONVERSION OF
PROTOPINES INTO BENZO[C]PHENANTHRIDINE ALKALOIDS 59 4.1.1.5. SYNTHESIS
OF SANGUINARINE VIA PSCHORR CYCLIZATION 60 4.1.2. SYNTHESIS OF THE
2,3,7,8,X-PENTASUBSTITUTED ALKALOIDS 61 4.1.2.1. SYNTHESIS OF THE
PENTASUBSTITUTED ALKALOIDS, CHELILUTINE, SANGUIRUBINE AND SANGUILUTINE
63 4.1.3. SYNTHESIS OF THE HEXASUBSTITUTED ALKALOID MACARPINE 65 4.1.4.
SYNTHESIS OF THE 2,3,8,9-TETRASUBSTITUTED ALKALOIDS 66 ~4.1.4.1.
SYNTHESIS OF AVICINE 66 4.1.4.2. SYNTHESIS OF NITIDINE 69 4.1.4.3.
SYNTHESIS OF FAGARONINE 72 4.2. TOTAL SYNTHESIS OF THE
B/C-HEXAHYDROBENZO[C]PHENANTHRIDINE ALKALOIDS 73 4.2.1. TOTAL SYNTHESIS
OF THE CHELIDONINE ALKALOIDS 74 4.2.1.1. SYNTHESIS OF CHELIDONINE 74
4.2.1.2. SYNTHESIS OF HOMOCHELIDONINE 77 4.2.2. TOTAL SYNTHESIS OF THE
CORYNOLINE ALKALOIDS 79 4.2.2.1. SYNTHESIS OF THE KEY INTERMEDIATE
11,12-DEHYDRO DERIVATIVES 80 4.2.2.2. SYNTHESIS OF CORYNOLINE 81
4.2.2.3. SYNTHESIS OF A CORYNOLINE ANALOGUE 82 5. PHARMACOLOGICAL
ACTIVITY OF BENZO[C]PHENANTHRIDINE ALKALOIDS AND RELATED COMPOUNDS 85 6.
FUTURE PERSPECTIVES 87 REFERENCES 88 F. SZTARICSKAI AND R. BOGNAR THE
CHEMISTRY OF THE VANCOMYCIN GROUP ) OF ANTIBIOTICS 1. INTRODUCTION 93 2.
GENERAL CHARACTERIZATION OF THE VANCOMYCIN GROUP OF ANTIBIOTICS 96
REFERENCES 100 3. VANCOMYCIN 103 3.1. ISOLATION 103 3.2. BIOLOGICAL
ACTIVITY, APPLICATION 103 3.3. STRUCTURAL STUDIES 104 3.3.1. HYDROLYSIS
104 3.3.2. CARBOHYDRATES 105 3.3.2.1. DEFINITIVE SYNTHESIS OF
VANCOSAMINE 109 CONTENTS 3.3.3. THE AGLYCONE OF VANCOMYCIN 110 3.3.3.1.
OXIDATIVE AND REDUCTIVE DEGRADATION 110 3.3.3.2. VANCOMYCINIC ACID ILL
3.3.3.3. ACTINOIDINIC ACID 115 3.4. MODE OF ACTION 120 REFERENCES 122 4.
ACTINOIDIN 124 4.1. ISOLATION 124 4.2. BIOLOGICAL ACTIVITY 124 4.3.
STRUCTURAL STUDIES 125 4.3.1. HYDROLYSIS 125 4.3.2. L-ACOSAMINE AND
L-ACTINOSAMINE 126 4.3.2.1. SYNTHESES OF L-ACOSAMINE AND L-ACTINOSAMINE
128 4.3.3. AGLYCONE 132 4.3.3.1. PHENYLGLYCINES 132 4.3.3.2.
ACTINOIDINIC ACID (AMINO ACID B) 134 4.3.3.3. MONODECHLOROVANCOMYCINIC
ACID 136 4.3.4. THE CARBOHYDRATE-AGLYCONE LINKAGES 138 REFERENCES 141 5.
AVOPARCIN 143 5.1. ISOLATION 143 5.2. BIOLOGICAL ACTIVITY AND
APPLICATION 143 5.3. STRUCTURAL STUDIES 144 5.3.1. AGLYCONE 144 5.3.2.
THE CARBOHYDRATE-AGLYCONE LINKAGES 147 REFERENCES 150 6.
RISTOCETIN-RISTOMYCIN 151 6.1. ISOLATION 151 6.2. BIOLOGICAL ACTIVITY
AND APPLICATION 152 6.3. STRUCTURAL STUDIES .. .. 153 6.3.1. HYDROLYSIS
;.. 153 6.3.2. CARBOHYDRATES 155 6.3.2.1. SEQUENTIAL ATTACHMENT OF
NEUTRAL SUGARS 155 6.3.2.2. SYNTHESIS OF RISTOBIOSE AND RISTOTRIOSE 159
6.3.2.3. RISTOSAMINE 161 6.3.2.3.1. SYNTHESIS OF L-RISTOSAMINE 163
6.3.2.3.2. SYNTHESIS OF D-RISTOSAMINE 167 6.3.3. AGLYCONE 171 6.3.3.1.
ACID HYDROLYSIS, HYDROGENOLYSIS 171 6.3.3.2. OXIDATION 174 6.3.3.3.
REDUCTIVE ALKALINE DEGRADATION AND DECOMPOSITION WITH SODIUM
HYPOCHLORITE 175 6.3.3.4. THE STRUCTURE OF THE AGLYCONE MOIETY 179
6.3.4. THE CARBOHYDRATE-AGLYCONE LINKAGES 184 6.4. MECHANISM OF
ANTIBIOTIC ACTION 191 REFERENCES 193 8 CONTENTS 7. ANTIBIOTIC COMPLEX
A-35512 196 7.1. ISOLATION 196 7.2. BIOLOGICAL ACTIVITY 196 7.3. ,
STRUCTURAL STUDIES 197 7.3.1. HYDROLYSIS 197 7.3.2. CARBOHYDRATES 198
7.3.3. AGLYCONE 199 7.3.3.1. OXIDATIVE DEGRADATION 199 7.4. MECHANISM OF
ACTION 201 REFERENCES . 201 INDEX TO SYNTHESES OF THE
BENZO[CJPHENANTHRIDINE ALKALOIDS 7 203 INDEX TO THE CHEMISTRY OF THE
VANCOMYCIN GROUP OF ANTIBIOTICS 205
|
| any_adam_object | 1 |
| author | Ninomiya, I. Naito, T. Sztaricskai, F. Bognár, R. |
| author_facet | Ninomiya, I. Naito, T. Sztaricskai, F. Bognár, R. |
| author_role | aut aut aut aut |
| author_sort | Ninomiya, I. |
| author_variant | i n in t n tn f s fs r b rb |
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| bvnumber | BV006700008 |
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| discipline | Chemie / Pharmazie |
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| genre | Vancomycin-Antibiotika gnd |
| genre_facet | Vancomycin-Antibiotika |
| id | DE-604.BV006700008 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T16:50:06Z |
| institution | BVB |
| isbn | 9630532557 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-004259959 |
| oclc_num | 633252483 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-20 DE-83 DE-11 |
| owner_facet | DE-355 DE-BY-UBR DE-20 DE-83 DE-11 |
| physical | 209 S. Ill. |
| psigel | TUB-nb |
| publishDate | 1984 |
| publishDateSearch | 1984 |
| publishDateSort | 1984 |
| publisher | Akad. Kiadó |
| record_format | marc |
| series | Recent developments in the chemistry of natural carbon compounds |
| series2 | Recent developments in the chemistry of natural carbon compounds |
| spelling | Ninomiya, I. Verfasser aut Syntheses of the benzo-c-phenanthridine alkaloids by I. Ninomiya and T. Naito Budapest Akad. Kiadó 1984 209 S. Ill. txt rdacontent n rdamedia nc rdacarrier Recent developments in the chemistry of natural carbon compounds 10 Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Benzophenanthridinalkaloide (DE-588)4334860-9 gnd rswk-swf Vancomycin-Antibiotika gnd rswk-swf Vancomycin-Antibiotika f DE-604 Benzophenanthridinalkaloide (DE-588)4334860-9 s Chemische Synthese (DE-588)4133806-6 s Naito, T. Verfasser aut Sztaricskai, F. aut The chemistry of the vancomycin group of antibiotics Bognár, R. aut The chemistry of the vancomycin group of antibiotics Recent developments in the chemistry of natural carbon compounds 10 (DE-604)BV006654905 10 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004259959&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis <<The>> chemistry of the vancomycin group of antibiotics by F. Sztaricskai and R. Bognár |
| spellingShingle | Ninomiya, I. Naito, T. Sztaricskai, F. Bognár, R. Syntheses of the benzo-c-phenanthridine alkaloids Recent developments in the chemistry of natural carbon compounds Chemische Synthese (DE-588)4133806-6 gnd Benzophenanthridinalkaloide (DE-588)4334860-9 gnd |
| subject_GND | (DE-588)4133806-6 (DE-588)4334860-9 |
| title | Syntheses of the benzo-c-phenanthridine alkaloids |
| title_alt | The chemistry of the vancomycin group of antibiotics |
| title_auth | Syntheses of the benzo-c-phenanthridine alkaloids |
| title_exact_search | Syntheses of the benzo-c-phenanthridine alkaloids |
| title_full | Syntheses of the benzo-c-phenanthridine alkaloids by I. Ninomiya and T. Naito |
| title_fullStr | Syntheses of the benzo-c-phenanthridine alkaloids by I. Ninomiya and T. Naito |
| title_full_unstemmed | Syntheses of the benzo-c-phenanthridine alkaloids by I. Ninomiya and T. Naito |
| title_short | Syntheses of the benzo-c-phenanthridine alkaloids |
| title_sort | syntheses of the benzo c phenanthridine alkaloids |
| topic | Chemische Synthese (DE-588)4133806-6 gnd Benzophenanthridinalkaloide (DE-588)4334860-9 gnd |
| topic_facet | Chemische Synthese Benzophenanthridinalkaloide Vancomycin-Antibiotika |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004259959&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV006654905 |
| work_keys_str_mv | AT ninomiyai synthesesofthebenzocphenanthridinealkaloids AT naitot synthesesofthebenzocphenanthridinealkaloids AT sztaricskaif synthesesofthebenzocphenanthridinealkaloids AT bognarr synthesesofthebenzocphenanthridinealkaloids |