Studies towards the total synthesis of cochinchistemonine:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
München
Verl. Dr. Hut
2011
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Organische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | 155 S. Ill., graph. Darst. |
| ISBN: | 9783868538168 |
Internformat
MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV037309639 | ||
| 003 | DE-604 | ||
| 005 | 20120217 | ||
| 007 | t | ||
| 008 | 110330s2011 ad|| m||| 00||| eng d | ||
| 020 | |a 9783868538168 |9 978-3-86853-816-8 | ||
| 035 | |a (OCoLC)724885006 | ||
| 035 | |a (DE-599)BVBBV037309639 | ||
| 040 | |a DE-604 |b ger |e rakwb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-91 |a DE-19 |a DE-12 |a DE-355 | ||
| 082 | 0 | |a 547.7 |2 22//ger | |
| 084 | |a CHE 624d |2 stub | ||
| 084 | |a CHE 692d |2 stub | ||
| 100 | 1 | |a Tassel, Jean |e Verfasser |0 (DE-588)144037831 |4 aut | |
| 245 | 1 | 0 | |a Studies towards the total synthesis of cochinchistemonine |c Jean Christian Germain Tassel |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a München |b Verl. Dr. Hut |c 2011 | |
| 300 | |a 155 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Organische Chemie | |
| 502 | |a Zugl.: München, Techn. Univ., Diss., 2011 | ||
| 650 | 0 | 7 | |a Schraubenbaumgewächse |0 (DE-588)4456916-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Alkaloide |0 (DE-588)4068543-3 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Alkaloide |0 (DE-588)4068543-3 |D s |
| 689 | 0 | 1 | |a Schraubenbaumgewächse |0 (DE-588)4456916-6 |D s |
| 689 | 0 | 2 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 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=022464098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-022464098 | ||
Datensatz im Suchindex
| _version_ | 1804145584295116800 |
|---|---|
| adam_text | IMAGE 1
TABLE OF CONTENTS
I. THEORETICAL SECTION 1
1. INTRODUCTION: ALKALOIDS OF THE STEMONA GENUS 1
2. A IM AND SCOPE OF THIS STUDY 4
2.1. COCHINCHISTEMONINE, AN UNUSUAL ALKALOID AS A TARGET MOLECULE 4
2.2. TOTAL SYNTHESIS OF ()-STEMONAMIDE REPORTED BY A. S. KENDE 6
2.3. AZEPINE FORMATION IN THE SYNTHESIS OF STEMONA ALKALOIDS 8
2.3.1. AZEPINE FORMATION BY SLAUDINGER-AZA-WITTIG REACTION 9
2.3.2. AZEPINE FORMATION BY 7-EXO-TET CYCLIZATION 10
2.3.3. AZEPINE FORMATION BY [4+2]-CYDOADDITION 11
2.3.4. AZEPINE FORMATION BY RING CLOSING METATHESIS (RCM) 11
2.4. RETROSYNTHETIC ANALYSIS OF COCHINCHISTEMONINE 12
2.4.1. VARIANT A 13
2.4.2. VARIANT B 14
3. ASYMMETRIC SYNTHESIS OF PRECURSOR 41 16
3.1. SYNTHESIS OFMESO CIS-2,6-DISUBSTITUTEDPIPERIDINE 51 16
3.2. ENZYMATIC DESYMMETRIZATION OFMESO CIS-2,6~SUBSTITUTED PIPERIDINE 51
17
3.3. NUCLEOPHILIC ADDITION OF A GRIGNARD REAGENT TO A-AMINO ALDEHYDE 55
19
3.4. PROOF OF THE RELATIVE CONFIGURATION OFALCOHOL 64 24
3.5. NUCLEOPHILIC ADDITION OF AN ETHYLZINC REAGENT TO A-AMINO ALDEHYDE
55 26
3.6. FUTURE RESEARCH 28
4. M O D EL STUDIES: THE ALDOL SPIROCYCLIZATION REACTION 29
4.1. INTRODUCTION 29
4.2. SYNTHESIS TOWARDS A MODEL SYSTEM FOR PRECURSOR 35 (VARIANT A) 29
4.2.1. RETROSYNTHETIC ANALYSIS OF SUBSTRATE 75 30
4.2.2. SYNTHESIS OF TETRONATE 37 30
4.2.3. ATTEMPTS TOWARDS THE SYNTHESIS OF FRAGMENT 76 31
4.2.4. SYNTHESIS OF PROTECTED FRAGMENT 84 33
4.2.5. COUPLING WITH TETRONATE 37 34
4.3. SYNTHESIS OFA MODEL SYSTEM FOR PRECURSOR 43 (VARIANT B) 35
4.3.1. SYNTHESIS OF PRECURSOR 93 36
4.3.2. SYNTHESIS OF SUBSTRATE 90 36
4.3.3. THE KEY ALDOL SPIROCYCLIZATION REACTION 37
5. M O D EL STUDIES: ROUTES TO THE PYRIDO[1,2- I]AZEPINE NUCLEUS 40
5.1. APPROACH VIA A DITHIANE CONJUGATE ADDITION 40
5.1.1. INTRODUCTION 40
5.1.2. RETROSYNTHETIC ANALYSIS OF SUBSTRATE 98 41
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1010570390
DIGITALISIERT DURCH
IMAGE 2
5.1.3. SYNTHESIS OF DILHIANE 101 42
5.1.4. SYNTHESIS OF AMINE 102 43
5.1.5. ATTEMPTED CYCLIZATION OF DITHIANE 98 44
5.2. APPROACH VIA A STETTER REACTION 45
5.2.1. INTRODUCTION 45
5.2.2. MODEL SYSTEM FOR SIX-MEMBERED RING FORMATION VIA AN
INTRAMOLECULAR STETTER REACTION 48
5.2.3. MODEL SYSTEM FOR SEVEN-MEMBERED RING FORMATION VIA AN
INTRAMOLECULAR STETTER REACTION 53
5.2.4. APPROACH VIA AN INTERMOLECULAR STETTER REACTION 68
5.3. FUTURE RESEARCH 70
6. SUMMARY 72
II. EXPERIMENTAL SECTION 77
1. GENERAL PROCEDURES 77
1.1. SOLVENTS AND REAGENTS 77
1.2. ANALYTICAL TECHNIQUES AND APPARATUS 78
2. PRECURSOR SYNTHESIS 81
3. MODEL SYSTEM FOR THE ALDOL SPIROCYCLIZATION REACTION 95
4. MODEL SYSTEM FOR THE FORMATION OF A PYRIDO[L,2-A]AZEPINE NUCLEUS 116
III. GLOSSARY 150
IV. REFERENCES 152
|
| any_adam_object | 1 |
| author | Tassel, Jean |
| author_GND | (DE-588)144037831 |
| author_facet | Tassel, Jean |
| author_role | aut |
| author_sort | Tassel, Jean |
| author_variant | j t jt |
| building | Verbundindex |
| bvnumber | BV037309639 |
| classification_tum | CHE 624d CHE 692d |
| ctrlnum | (OCoLC)724885006 (DE-599)BVBBV037309639 |
| 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 Chemie |
| edition | 1. Aufl. |
| format | Thesis Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01708nam a2200433 c 4500</leader><controlfield tag="001">BV037309639</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20120217 </controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">110330s2011 ad|| m||| 00||| eng d</controlfield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783868538168</subfield><subfield code="9">978-3-86853-816-8</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)724885006</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)BVBBV037309639</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-91</subfield><subfield code="a">DE-19</subfield><subfield code="a">DE-12</subfield><subfield code="a">DE-355</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">CHE 624d</subfield><subfield code="2">stub</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">CHE 692d</subfield><subfield code="2">stub</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Tassel, Jean</subfield><subfield code="e">Verfasser</subfield><subfield code="0">(DE-588)144037831</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Studies towards the total synthesis of cochinchistemonine</subfield><subfield code="c">Jean Christian Germain Tassel</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">2011</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">155 S.</subfield><subfield code="b">Ill., graph. Darst.</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, Techn. Univ., Diss., 2011</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Schraubenbaumgewächse</subfield><subfield code="0">(DE-588)4456916-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Asymmetrische Synthese</subfield><subfield code="0">(DE-588)4135603-2</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Alkaloide</subfield><subfield code="0">(DE-588)4068543-3</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">Alkaloide</subfield><subfield code="0">(DE-588)4068543-3</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Schraubenbaumgewächse</subfield><subfield code="0">(DE-588)4456916-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="2"><subfield code="a">Asymmetrische Synthese</subfield><subfield code="0">(DE-588)4135603-2</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</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=022464098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-022464098</subfield></datafield></record></collection> |
| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV037309639 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T23:21:46Z |
| institution | BVB |
| isbn | 9783868538168 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-022464098 |
| oclc_num | 724885006 |
| open_access_boolean | |
| owner | DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-12 DE-355 DE-BY-UBR |
| owner_facet | DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-12 DE-355 DE-BY-UBR |
| physical | 155 S. Ill., graph. Darst. |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Verl. Dr. Hut |
| record_format | marc |
| series2 | Organische Chemie |
| spelling | Tassel, Jean Verfasser (DE-588)144037831 aut Studies towards the total synthesis of cochinchistemonine Jean Christian Germain Tassel 1. Aufl. München Verl. Dr. Hut 2011 155 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Chemie Zugl.: München, Techn. Univ., Diss., 2011 Schraubenbaumgewächse (DE-588)4456916-6 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Alkaloide (DE-588)4068543-3 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Alkaloide (DE-588)4068543-3 s Schraubenbaumgewächse (DE-588)4456916-6 s Asymmetrische Synthese (DE-588)4135603-2 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=022464098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Tassel, Jean Studies towards the total synthesis of cochinchistemonine Schraubenbaumgewächse (DE-588)4456916-6 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Alkaloide (DE-588)4068543-3 gnd |
| subject_GND | (DE-588)4456916-6 (DE-588)4135603-2 (DE-588)4068543-3 (DE-588)4113937-9 |
| title | Studies towards the total synthesis of cochinchistemonine |
| title_auth | Studies towards the total synthesis of cochinchistemonine |
| title_exact_search | Studies towards the total synthesis of cochinchistemonine |
| title_full | Studies towards the total synthesis of cochinchistemonine Jean Christian Germain Tassel |
| title_fullStr | Studies towards the total synthesis of cochinchistemonine Jean Christian Germain Tassel |
| title_full_unstemmed | Studies towards the total synthesis of cochinchistemonine Jean Christian Germain Tassel |
| title_short | Studies towards the total synthesis of cochinchistemonine |
| title_sort | studies towards the total synthesis of cochinchistemonine |
| topic | Schraubenbaumgewächse (DE-588)4456916-6 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Alkaloide (DE-588)4068543-3 gnd |
| topic_facet | Schraubenbaumgewächse Asymmetrische Synthese Alkaloide Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=022464098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT tasseljean studiestowardsthetotalsynthesisofcochinchistemonine |