From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
München
Verl. Dr. Hut
2013
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Organische Chemie
|
| Schlagworte: | |
| Online-Zugang: | kostenfrei https://nbn-resolving.org/urn:nbn:de:bvb:19-153975 Inhaltsverzeichnis |
| Beschreibung: | XV, 326 S. graph. Darst. 210 mm x 148 mm, 517 g |
| ISBN: | 9783843908115 3843908117 |
Internformat
MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV040788432 | ||
| 003 | DE-604 | ||
| 005 | 20131015 | ||
| 007 | t | ||
| 008 | 130228s2013 gw d||| m||| 00||| eng d | ||
| 015 | |a 13,N07 |2 dnb | ||
| 016 | 7 | |a 1030510423 |2 DE-101 | |
| 020 | |a 9783843908115 |c Pb. : EUR 57.00 (DE), EUR 58.60 (AT), sfr 75.90 (freier Pr.) |9 978-3-8439-0811-5 | ||
| 020 | |a 3843908117 |9 3-8439-0811-7 | ||
| 024 | 3 | |a 9783843908115 | |
| 035 | |a (OCoLC)828821146 | ||
| 035 | |a (DE-599)DNB1030510423 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c XA-DE-BY | ||
| 049 | |a DE-19 |a DE-12 |a DE-355 |a DE-384 |a DE-473 |a DE-703 |a DE-1051 |a DE-824 |a DE-29 |a DE-91 |a DE-1049 |a DE-92 |a DE-739 |a DE-898 |a DE-706 |a DE-20 |a DE-1102 | ||
| 082 | 0 | |a 547.7 |2 22/ger | |
| 084 | |a 540 |2 sdnb | ||
| 100 | 1 | |a Hager, Dominik |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides |c Dominik Hager |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a München |b Verl. Dr. Hut |c 2013 | |
| 300 | |a XV, 326 S. |b graph. Darst. |c 210 mm x 148 mm, 517 g | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Organische Chemie | |
| 502 | |a Zugl.: München, Univ., Diss., 2012 | ||
| 650 | 0 | 7 | |a Totalsynthese |0 (DE-588)4412308-5 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Naturstoff |0 (DE-588)4041418-8 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Naturstoff |0 (DE-588)4041418-8 |D s |
| 689 | 0 | 1 | |a Totalsynthese |0 (DE-588)4412308-5 |D s |
| 689 | 0 | |5 DE-604 | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe |o urn:nbn:de:bvb:19-153975 |
| 856 | 4 | 1 | |u http://edoc.ub.uni-muenchen.de/15397/ |x Verlag |z kostenfrei |3 Volltext |
| 856 | 4 | |u https://nbn-resolving.org/urn:nbn:de:bvb:19-153975 |x Resolving-System | |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025766628&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 912 | |a ebook | ||
| 999 | |a oai:aleph.bib-bvb.de:BVB01-025766628 | ||
Datensatz im Suchindex
| _version_ | 1804150119448182784 |
|---|---|
| adam_text | IMAGE 1
TABLE OF CONTENTS
TABLE OF CONTENTS
ABSTRACT ............- I
SUMMARY HI
ACKNOWLEDGEMENTS... VII
ABBREVIATIONS IX
TABLE OF CONTENTS XIII
CHAPTER I: THE TOTAL SYNTHESIS OF HERBICIDIN C AND AUREONUCLEMYCIN
1. INTRODUCTION 1
2. ISOLATION, BIOLOGY AND STRUCTURAL FEATURES OF THE HERBICIDIN FAMILY 5
3. PREVIOUS WORK ON HERBICIDINS...... 6
3.1. UNSUCCESSFUL C 6PLUS CJ APPROACHES TOWARD THE HERBICIDIN BACKBONE 6
3.2. ICHIKAWA S TOTAL SYNTHESIS OF HERBICIDIN B THROUGH EARLY-STAGE
GLYCOSYLATION.... 10
4. THE RIGHT SIDE APPROACH: A PRELIMINARY STUDY .......... ..........
........ 13
4.1. RETROSYNTHETIC ANALYSIS AND STRATEGY OF THE RIGHT SIDE APPROACH 13
4.2. RESULTS AND DISCUSSION OF THE RIGHT SIDE APPROACH - SYNTHESIS OF
THE
CARBOHYDRATE BACKBONE 14
5. THE LEFT SIDE APPROACH......... ......................
.................. ..............-.... 19
5.1. RETROSYNTHETIC ANALYSIS AND STRATEGY OF THE LEFT SIDE APPROACH 19
5.2. RESULTS AND DISCUSSION OF THE LEFT SIDE APPROACH - TOTAL SYNTHESIS
OF
HERBICIDIN C AND AUREONUCLEMYCIN 19
6. PREPARATION OF COMPOUNDS FOR SAR STUDY WITH BAYER CROPSCIENCE
AG........ 29
6.1. DERIVATIZATION OF HERBICIDIN A 30
6.2. DERIVATIVES FROM THE RIGHT SIDE APPROACH 33
6.3. DERIVATIVES FROM THE LEFT SIDE APPROACH 34
7. CONCLUSIONS 36
XNI
HTTP://D-NB.INFO/1030510423
IMAGE 2
TABLE OF CONTENTS
CHAPTER II: SYNTHESIS TOWARD THE ALKALOID STEPHADIAMINE
8. INTRODUCTION............. ............................. .........
....... ......... ....... ..........37
9. ISOLATION, BIOLOGY AND PROPERTIES OF STEPHADIAMINE 40
9.1. ISOLATION AND STRUCTURE 40
9.2. BIOSYNTHETIC CONSIDERATIONS 42
10. RESULTS AND DISCUSSION - TOWARD STEPHADIAMINE 44
10.1. STRATEGY AND RETROSYNTHETIC ANALYSIS OF STEPHADIAMINE 44
10.2. ASSEMBLY OF P-TETRALONE 45
10.3. TOWARD TRICYCLIC ENAMINE 47
10.3.1. PREVIOUS WORK ON THE FORMATION OF THE KEY ENAMINE 47
10.3.2. STUDIES TOWARD ENAMINE SYSTEM 48
11. SUMMARY, CONCLUSIONS AND FUTURE DIRECTIONS........ 54
CHAPTER III: SYNTHETIC STUDIES TOWARD DIVERGOLIDES C AND D
12. INTRODUCTION... .......... ...............
.......................... .......... ........ ......... ...57
13. ISOLATION, BIOLOGY AND STRUCTURAL FEATURES OF THE DIVERGOLIDE FAMILY
61
14. RESULTS AND DISCUSSION OF THE SYNTHETIC STUDIES TOWARD DIVERGOLIDES
C AND D 65
14.1. RETROSYNTHETIC ANALYSIS FOR DIVERGOLIDE C AND D 65
14.2. ATTACHMENT OF THE WESTERN SIDE CHAIN 66
14.2.1. FIRST STRATEGY 66
14.2.2. SECOND STRATEGY 67
14.3. ATTACHMENT OF THE EASTERN SIDE CHAIN 71
14.4. TARGETING THE ACYL MIGRATION 72
15. CONCLUSIONS AND FURTHER WORK.......... .........
............................ .......... ........... 74
XIV
IMAGE 3
TABLE OF CONTENTS
CHAPTER IV: SYNTHESIS OF A BACTERIAL SIGNALING MOLECULE
16. INTRODUCTION 77
17. AUTOINDUCER REGULATORY CIRCUITS IN V. CHOLERAE AND L. PNEUMOPHILA 79
17.1. QUORUM SENSING IN V. CHOLERAE 79
17.2. QUORUM SENSING IN L. PNEUMOPHILA 80
18. SYNTHESIS OF LAI-1 .............. ............ ..........- 82
19. CONCLUSIONS AND OUTLOOK..... ........... ......... ............
.......... ..... 82
CHAPTER V: EXPERIMENTAL PROCEDURES AND ANALYTICAL DATA
20. GENERAL EXPERIMENTAL SECTION 83
21. EXPERIMENTAL PROCEDURES 85
21.1. EXPERIMENTAL DATA OF CHAPTER 1 85
21.2. EXPERIMENTAL DATA OF CHAPTER II 172
21.3. EXPERIMENTAL DATA OF CHAPTER III 177
21.4. EXPERIMENTAL DATA OF CHAPTER IV 195
22. APPENDICES.......... 200
22.1. NMR SPECTRA OF CHAPTER 1 200
22.2. NMR SPECTRA OF CHAPTER N 272
22.3. NMR SPECTRA OF CHAPTER III 277
22.4. NMR SPECTRA OF CHAPTER IV 295
22.5. SINGLE-CRYSTAL X-RAY ANALYSIS 299
22.6. COMPOUNDS SENT TO BAYER CROPSCIENCE AG FOR SAR STUDY 316
23. LITERATURE.... ..............
................-..............................-................-.........321
XV
|
| any_adam_object | 1 |
| author | Hager, Dominik |
| author_facet | Hager, Dominik |
| author_role | aut |
| author_sort | Hager, Dominik |
| author_variant | d h dh |
| building | Verbundindex |
| bvnumber | BV040788432 |
| collection | ebook |
| ctrlnum | (OCoLC)828821146 (DE-599)DNB1030510423 |
| dewey-full | 547.7 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.7 |
| dewey-search | 547.7 |
| dewey-sort | 3547.7 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| edition | 1. Aufl. |
| format | Thesis Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>02172nam a2200505 c 4500</leader><controlfield tag="001">BV040788432</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20131015 </controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">130228s2013 gw d||| m||| 00||| eng d</controlfield><datafield tag="015" ind1=" " ind2=" "><subfield code="a">13,N07</subfield><subfield code="2">dnb</subfield></datafield><datafield tag="016" ind1="7" ind2=" "><subfield code="a">1030510423</subfield><subfield code="2">DE-101</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783843908115</subfield><subfield code="c">Pb. : EUR 57.00 (DE), EUR 58.60 (AT), sfr 75.90 (freier Pr.)</subfield><subfield code="9">978-3-8439-0811-5</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">3843908117</subfield><subfield code="9">3-8439-0811-7</subfield></datafield><datafield tag="024" ind1="3" ind2=" "><subfield code="a">9783843908115</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)828821146</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)DNB1030510423</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakddb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="044" ind1=" " ind2=" "><subfield code="a">gw</subfield><subfield code="c">XA-DE-BY</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-19</subfield><subfield code="a">DE-12</subfield><subfield code="a">DE-355</subfield><subfield code="a">DE-384</subfield><subfield code="a">DE-473</subfield><subfield code="a">DE-703</subfield><subfield code="a">DE-1051</subfield><subfield code="a">DE-824</subfield><subfield code="a">DE-29</subfield><subfield code="a">DE-91</subfield><subfield code="a">DE-1049</subfield><subfield code="a">DE-92</subfield><subfield code="a">DE-739</subfield><subfield code="a">DE-898</subfield><subfield code="a">DE-706</subfield><subfield code="a">DE-20</subfield><subfield code="a">DE-1102</subfield></datafield><datafield tag="082" ind1="0" ind2=" "><subfield code="a">547.7</subfield><subfield code="2">22/ger</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">540</subfield><subfield code="2">sdnb</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Hager, Dominik</subfield><subfield code="e">Verfasser</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides</subfield><subfield code="c">Dominik Hager</subfield></datafield><datafield tag="250" ind1=" " ind2=" "><subfield code="a">1. Aufl.</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">München</subfield><subfield code="b">Verl. Dr. Hut</subfield><subfield code="c">2013</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">XV, 326 S.</subfield><subfield code="b">graph. Darst.</subfield><subfield code="c">210 mm x 148 mm, 517 g</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="490" ind1="0" ind2=" "><subfield code="a">Organische Chemie</subfield></datafield><datafield tag="502" ind1=" " ind2=" "><subfield code="a">Zugl.: München, Univ., Diss., 2012</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Totalsynthese</subfield><subfield code="0">(DE-588)4412308-5</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Naturstoff</subfield><subfield code="0">(DE-588)4041418-8</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="655" ind1=" " ind2="7"><subfield code="0">(DE-588)4113937-9</subfield><subfield code="a">Hochschulschrift</subfield><subfield code="2">gnd-content</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Naturstoff</subfield><subfield code="0">(DE-588)4041418-8</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Totalsynthese</subfield><subfield code="0">(DE-588)4412308-5</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="776" ind1="0" ind2="8"><subfield code="i">Erscheint auch als</subfield><subfield code="n">Online-Ausgabe</subfield><subfield code="o">urn:nbn:de:bvb:19-153975</subfield></datafield><datafield tag="856" ind1="4" ind2="1"><subfield code="u">http://edoc.ub.uni-muenchen.de/15397/</subfield><subfield code="x">Verlag</subfield><subfield code="z">kostenfrei</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="856" ind1="4" ind2=" "><subfield code="u">https://nbn-resolving.org/urn:nbn:de:bvb:19-153975</subfield><subfield code="x">Resolving-System</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">DNB Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025766628&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ebook</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-025766628</subfield></datafield></record></collection> |
| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV040788432 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T00:33:51Z |
| institution | BVB |
| isbn | 9783843908115 3843908117 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-025766628 |
| oclc_num | 828821146 |
| open_access_boolean | 1 |
| owner | DE-19 DE-BY-UBM DE-12 DE-355 DE-BY-UBR DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-91 DE-BY-TUM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-706 DE-20 DE-1102 |
| owner_facet | DE-19 DE-BY-UBM DE-12 DE-355 DE-BY-UBR DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-91 DE-BY-TUM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-706 DE-20 DE-1102 |
| physical | XV, 326 S. graph. Darst. 210 mm x 148 mm, 517 g |
| psigel | ebook |
| publishDate | 2013 |
| publishDateSearch | 2013 |
| publishDateSort | 2013 |
| publisher | Verl. Dr. Hut |
| record_format | marc |
| series2 | Organische Chemie |
| spelling | Hager, Dominik Verfasser aut From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides Dominik Hager 1. Aufl. München Verl. Dr. Hut 2013 XV, 326 S. graph. Darst. 210 mm x 148 mm, 517 g txt rdacontent n rdamedia nc rdacarrier Organische Chemie Zugl.: München, Univ., Diss., 2012 Totalsynthese (DE-588)4412308-5 gnd rswk-swf Naturstoff (DE-588)4041418-8 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Naturstoff (DE-588)4041418-8 s Totalsynthese (DE-588)4412308-5 s DE-604 Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:19-153975 http://edoc.ub.uni-muenchen.de/15397/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:19-153975 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025766628&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Hager, Dominik From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| subject_GND | (DE-588)4412308-5 (DE-588)4041418-8 (DE-588)4113937-9 |
| title | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides |
| title_auth | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides |
| title_exact_search | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides |
| title_full | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides Dominik Hager |
| title_fullStr | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides Dominik Hager |
| title_full_unstemmed | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides Dominik Hager |
| title_short | From nucleosides to alkaloids and polyketides: Total synthesis of herbicidin C and studies toward stephadiamine and divergolides |
| title_sort | from nucleosides to alkaloids and polyketides total synthesis of herbicidin c and studies toward stephadiamine and divergolides |
| topic | Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| topic_facet | Totalsynthese Naturstoff Hochschulschrift |
| url | http://edoc.ub.uni-muenchen.de/15397/ https://nbn-resolving.org/urn:nbn:de:bvb:19-153975 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025766628&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT hagerdominik fromnucleosidestoalkaloidsandpolyketidestotalsynthesisofherbicidincandstudiestowardstephadiamineanddivergolides |