Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2011
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| Schlagworte: | |
| Online-Zugang: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-229140 Inhaltsverzeichnis |
| Beschreibung: | 192 S. Ill., graph. Darst. |
Internformat
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| 264 | 1 | |c 2011 | |
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Datensatz im Suchindex
| _version_ | 1817492186886832128 |
|---|---|
| adam_text |
IMAGE 1
CONTENTS
1. INTRODUCTION : 1
1.1. A,P-UNSATURATED CARBONYL COMPOUNDS AND INFLAMMATION 1
1.2. EXAMPLES O F A,P-UNSATURATED PHYTOCHEMICALS FOR THERAPEUTIC
APPLICATIONS 5
1.3. FINE TUNING THE MICHAEL ACCEPTOR ACTIVITY 7
1.4. * LIMNOPHILASPIROKETONE AS A POINT FOR INSPIRATION 9
1.5. NATURAL PRODUCTS WITH A 3(2//)-FURANONE MOIETY 10
1.6. APPROACHES FOR THE SYNTHESIS O F 3(2//)-FURANONES 12
2. AIM O F THE PRESENT STUDY 22
3. RESULTS AND DISCUSSION 23
3.1. RETROSYNTHETIC APPROACH TOWARDS THE TOTAL SYNTHESIS O F
LIMNOPHILASPIROKETONE 2 3
3.2. SYNTHESIS O F THE CHIRAL CYCLOPENTYL BUILDING BLOCK 77 26
3.2.1. INTRODUCTION O F AN ACETYLENE FUNCTIONALITY 26
3.2.2. ASYMMETRIC EPOXIDATION REACTIONS 27
3.2.3. ASYMMETRIC CYANOHYDRIN REACTIONS 35
3.3. SUBSEQUENT TRANSFORMATIONS ON THE CHIRAL BUILDING BLOCK 77 4 0
3.3.1. DIFFERENTIATION O F THE TMS ETHER AND TMS ACETYLENE 41
3.3.2. COUPLING REACTIONS WITH BENZALDEHYDE AND BENZOIC ACID DERIVATIVES
4 4
3.3.3. RING OPENING REACTIONS ON THE EPOXIDE 4 6
3.3.4. HYDROLYSIS AND PROTECTING GROUP MANIPULATIONS ON THE CYANOHYDRIN
4 9
3.4. LIMNO-CP - A NATURAL PRODUCT DERIVED MODEL SUBSTRATE 56
3.4.1. SYNTHESIS O F /PR-LIMNO-CP 57
3.4.2. INVESTIGATIONS ON THE FORMATION O F THE SPIROCYCLIC FRAMEWORK 58
3.5. SYNTHESIS O F A-SUBSTITUTED DERIVATIVES O F LIMNO-CP 60
3.5.1. INTRODUCTION O F HALOGENS 61
3.5.2. INTRODUCTION O F CARBON BASED SUBSTITUENTS 66
3.5.3. INTRODUCTION O F OXYGEN BASED SUBSTITUENTS 70
3.5.4. METALATION APPROACHES 72
3.5.5. DEPROTECTION REACTIONS 77
3.6. 1,2- VERSUS 1,4-ADDITION O F NUCLEOPHILES 78
3.6.1. 1,2-ADDITION 78
3.6.2. 1,4-ADDITION 83
HTTP://D-NB.INFO/1028521537
IMAGE 2
3.6.3. N M R ANALYSIS O F THE SUBSTITUTION EFFECTS ON THE MICHAEL
ACCEPTOR ACTIVITY 84
4. SUMMARY. . . 87
5. EXPERIMENTAL PART 92
5.1. GENERAL METHODS AND MATERIALS 92
5.2. EXPERIMENTAL PROCEDURES 94
6. APPENDIX 135
6.1. NMR SPECTRA 135
6.2. G C SPECTRA 178
6.3. X-RAY DATA 179
7. REFERENCES. 182
CURRICULUM VITAE 189
ACKNOWLEDGEMENTS 191 |
| any_adam_object | 1 |
| author | Lindner, Simon 1982- |
| author_GND | (DE-588)1027458564 |
| author_facet | Lindner, Simon 1982- |
| author_role | aut |
| author_sort | Lindner, Simon 1982- |
| author_variant | s l sl |
| building | Verbundindex |
| bvnumber | BV040518729 |
| classification_rvk | VK 5075 |
| collection | ebook |
| ctrlnum | (OCoLC)820376754 (DE-599)BVBBV040518729 |
| discipline | Chemie / Pharmazie |
| format | Thesis Book |
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| physical | 192 S. Ill., graph. Darst. |
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| spelling | Lindner, Simon 1982- Verfasser (DE-588)1027458564 aut Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP vorgelegt von Simon Lindner 2011 192 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2011 Alpha-beta-ungesättigte Verbindungen (DE-588)4430751-2 gnd rswk-swf Carbonylverbindungen (DE-588)4147318-8 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Spiroketone (DE-588)4282324-9 gnd rswk-swf Naturstoff (DE-588)4041418-8 gnd rswk-swf Wegerichgewächse (DE-588)4189369-4 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Wegerichgewächse (DE-588)4189369-4 s Spiroketone (DE-588)4282324-9 s Chemische Synthese (DE-588)4133806-6 s DE-604 Carbonylverbindungen (DE-588)4147318-8 s Alpha-beta-ungesättigte Verbindungen (DE-588)4430751-2 s Naturstoff (DE-588)4041418-8 s Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-229140 http://epub.uni-regensburg.de/22914/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-229140 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025365073&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Lindner, Simon 1982- Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP Alpha-beta-ungesättigte Verbindungen (DE-588)4430751-2 gnd Carbonylverbindungen (DE-588)4147318-8 gnd Chemische Synthese (DE-588)4133806-6 gnd Spiroketone (DE-588)4282324-9 gnd Naturstoff (DE-588)4041418-8 gnd Wegerichgewächse (DE-588)4189369-4 gnd |
| subject_GND | (DE-588)4430751-2 (DE-588)4147318-8 (DE-588)4133806-6 (DE-588)4282324-9 (DE-588)4041418-8 (DE-588)4189369-4 (DE-588)4113937-9 |
| title | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP |
| title_auth | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP |
| title_exact_search | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP |
| title_full | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP vorgelegt von Simon Lindner |
| title_fullStr | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP vorgelegt von Simon Lindner |
| title_full_unstemmed | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP vorgelegt von Simon Lindner |
| title_short | Studies towards the total synthesis of Limnophilaspiroketone and the synthesis of alpha-modified enones of natural product derived model compound Limno-CP |
| title_sort | studies towards the total synthesis of limnophilaspiroketone and the synthesis of alpha modified enones of natural product derived model compound limno cp |
| topic | Alpha-beta-ungesättigte Verbindungen (DE-588)4430751-2 gnd Carbonylverbindungen (DE-588)4147318-8 gnd Chemische Synthese (DE-588)4133806-6 gnd Spiroketone (DE-588)4282324-9 gnd Naturstoff (DE-588)4041418-8 gnd Wegerichgewächse (DE-588)4189369-4 gnd |
| topic_facet | Alpha-beta-ungesättigte Verbindungen Carbonylverbindungen Chemische Synthese Spiroketone Naturstoff Wegerichgewächse Hochschulschrift |
| url | http://epub.uni-regensburg.de/22914/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-229140 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025365073&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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