More dead ends and detours: en route to successful total synthesis
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| Main Authors: | , , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2013
|
| Subjects: | |
| Online Access: | Cover Inhaltsverzeichnis |
| Physical Description: | XXI, 266 S. graph. Darst. |
| ISBN: | 9783527329762 9783527654628 |
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MARC
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Record in the Search Index
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| adam_text | IMAGE 1
V I I
CONTENTS
FOREWORD XIII PREFACE XVII
ABBREVIATIONS AND ACRONYMS X I X
1 INTRODUCTION 1
1.1 INTERMEDIATE IN THE TOTAL SYNTHESIS OF BREVETOXIN A 3 1.1.1 TARGET
RELEVANCE 4
1.1.2 SYNTHETIC PLANNING FOR BREVETOXIN A (1.1) 4 1.1.3 SYNTHETIC
PLANNING OF ALDEHYDE 1.4 5 1.1.4 PREDICTABLE PROBLEMS 5
1.1.5 SYNTHESIS OF 1.4 5
1.1.6 DISCUSSION 8
REFERENCES 12
2 THE INERTIA O F CONVENTIONAL FUNCTIONAL CROUPS 15
2.1 WELWITINDOLINONE A ISONITRILE 15 2.1.1 TARGET RELEVANCE 16 2.1.2
SYNTHETIC PLANNING 16 2.1.3 PREDICTABLE PROBLEMS 16
2.1.4 SYNTHESIS 17
2.1.5 DISCUSSION 24
2.2 OVERPROTECTING-MAVERICK PROTECTING GROUPS 26 2.2.1 IEJIMALIDES A-D
27
2.2.2 TARGET RELEVANCE 27 2.2.3 SYNTHETIC PLANNING 27 2.2.4 PREDICTABLE
PROBLEMS 28 2.2.5 SYNTHESIS 29
2.2.6 DISCUSSION 35
REFERENCES 37
HTTP://D-NB.INFO/1028051107
IMAGE 2
V I M [ CONTENTS
3 THE DIELS-ALDER REACTION 39
3.1 (-)-PLATENSIMYCIN 40
3.1.1 TARGET RELEVANCE 40
3.1.2 SYNTHETIC PLANNING FOR (-)-PLATINSIMYCIN (3.1) 40 3.1.3
PREDICTABLE PROBLEMS 40 3.1.4 DISCUSSION 46
3.2 STEPHACIDINS A AND B 49
3.2.1 TARGET RELEVANCE 49 3.2.2 SYNTHETIC PLANNING FOR ENT-STEPHACIDINS
A AND B 50 3.2.3 PREDICTABLE PROBLEMS 50
3.2.4 SYNTHESIS 51
3.2.5 DISCUSSION 54
REFERENCES 58
4 THE ALDOL CONDENSATION 61
4.1 THE ABC RING MOIETY OF (-)-NORZOANTHAMINE 62 4.1.1 TARGET RELEVANCE
62
4.1.2 SYNTHETIC PLANNING FOR (-)-NORZOANTHAMINE (4.1) 62 4.1.3
PREDICTABLE PROBLEMS 63 4.1.4 SYNTHESIS 63
4.1.5 DISCUSSION 68
4.2 (+)-TMC-151C 71
4.2.1 TARGET RELEVANCE 71
4.2.2 SYNTHETIC PLANNING FOR (+)-TMC-151C (4.30) 72 4.2.3 SYNTHESIS 73
4.2.4 DISCUSSION 75
REFERENCES 80
5 CYCLIZATIONS: CONCERTED, RADICAL, O R POLAR? 83
5.1 ()-MERRILACTONE A 85
5.1.1 TARGET RELEVANCE 85
5.1.2 SYNTHETIC PLANNING 85
5.1.3 PREDICTABLE PROBLEMS 86 5.1.4 SYNTHESIS 86
5.1.5 DISCUSSION 89
5.2 (-)-PSEUDOLARIC ACID B 92 5.2.1 TARGET RELEVANCE 93
5.2.2 SYNTHETIC PLANNING 93 5.2.3 PREDICTABLE PROBLEMS 94 5.2.4
SYNTHESIS 94
5.2.5 DISCUSSION 102
5.3 FORMAL SYNTHESIS OF PLATENSIMYCIN 104 5.3.1 TARGET RELEVANCE 104
5.3.2 SYNTHETIC PLANNING 104 5.3.3 PREDICTABLE PROBLEMS 105
IMAGE 3
CONTENTS | I X
5.3.4 SYNTHESIS 105
5.3.5 DISCUSSION 107
REFERENCES 110
6 MACROCODES: FROM RELUCTANT RING CLOSURE T O RELUCTANT RING OPENING 113
6.1 USTILOXIN D 114
6.1.1 TARGET RELEVANCE 114 6.1.2 SYNTHETIC PLANNING FOR USTILOXIN D 115
6.1.3 PREDICTABLE PROBLEMS 115 6.1.4 SYNTHESIS OF USTILOXIN D 116 6.1.5
DISCUSSION 118
6.2 LARGAZOLE 123
6.2.1 TARGET RELEVANCE 123 6.2.2 SYNTHETIC PLANNING FOR LARGAZOLE (6.36)
123 6.2.3 PREDICTABLE PROBLEMS 124
6.2.4 SYNTHESIS OF LARGAZOLE (6.36) 125 6.2.5 DISCUSSION 129
6.2.6 KEY SYNTHETIC REACTION 133 REFERENCES 134
7 STEREOCHEMISTRY, CONTROLLED OR UNCONTROLLED? 137
7.1 (-)-SAMADERIN Y 138
7.1.1 TARGET RELEVANCE 138 7.1.2 SYNTHETIC PLANNING 139 7.1.3
PREDICTABLE PROBLEMS 139 7.1.4 SYNTHESIS 139
7.1.5 DISCUSSION 145
7.2 ()-LYCONADIN A 148
7.2.1 TARGET RELEVANCE 148 7.2.2 SYNTHETIC PLANNING 148 7.2.3
PREDICTABLE PROBLEMS 149
7.2.4 SYNTHESIS 149
7.2.5 DISCUSSION 152
7.3 VANNUSAL B 154
7.3.1 TARGET RELEVANCE 154 7.3.2 SYNTHETIC PLANNING FOR THE ORIGINALLY
ASSIGNED STRUCTURE OF VANNUSAL B (7.58) 155
7.3.3 PREDICTABLE PROBLEMS 156 7.3.4 SYNTHESIS OF THE ORIGINALLY
ASSIGNED STRUCTURE OF VANNUSAL B (7.58) 156 7.3.5 SYNTHESIS OF VANNUSAL
B (7.56) 159 7.3.6 DISCUSSION 161
REFERENCES 166
IMAGE 4
X CONTENTS
8 TRANSITION METAL-MEDIATED TRANSFORMATIONS VS CONVENTIONAL
REACTIONS 169
8.1 BLUMIOLIDEC 170
8.1.1 TARGET RELEVANCE 171 8.1.2 SYNTHETIC PLANNING FOR BLUMIOLIDE C
(8.1) 171 8.1.3 SYNTHESIS 171
8.1.4 DISCUSSION 174
8.2 ARYLOMYCINA2 179
8.2.1 TARGET RELEVANCE 179 8.2.2 SYNTHETIC PLANNING 180
8.2.3 PREDICTABLE PROBLEMS 180 8.2.4 SYNTHESIS 180
8.2.5 DISCUSSION 184
8.3 (-)-STRYCHNINE 189
8.3.1 TARGET RELEVANCE . 189 8.3.2 SYNTHETIC PLANNING 190
8.3.3 PREDICTABLE PROBLEMS 190 8.3.4 SYNTHESIS OF (-)-STRYCHNINE 191
8.3.5 DISCUSSION 195
REFERENCES 198
9 WHEN METATHESIS FAILS 201
9.1 (+)-SAXITOXIN 202
9.1.1 TARGET RELEVANCE 202
9.1.2 SYNTHETIC PLANNING 203 9.1.3 PREDICTABLE PROBLEMS 204 9.1.4
SYNTHESIS OF (+)-SAXITOXIN 204 9.1.5 DISCUSSION 208
9.2 LAULIMALIDE FAMILY 211
9.2.1 TARGET RELEVANCE 211 9.2.2 SYNTHETIC PLANNING 213 9.2.3 SYNTHESIS
214
9.2.4 DISCUSSION 219
REFERENCES 222
10 OXIDATIONS IN C - C BOND BUILDING 225
10.1 CORTISTATINS A AND J 226
10.1.1 TARGET RELEVANCE 226 10.1.2 SYNTHETIC PLANNING FOR CORTISTATINS A
(10.1) AND J (10.2) 226 10.1.3 PREDICTABLE PROBLEMS 227
10.1.4 SYNTHESIS 227
10.1.5 DISCUSSION 232
10.2 GAMBIEROL ABC MOIETY 236 10.2.1 TARGET RELEVANCE 236 10.2.2
SYNTHETIC PLANNING 236
IMAGE 5
CONTENTS I X I
10.2.3 PREDICTABLE PROBLEMS 238
10.2.4 SYNTHESIS 238
10.2.5 DISCUSSION 243
REFERENCES 248
11 THE FAILURE O F EPOXIDE RING OPENING AND T H E LIMITS O F CASCADE
REACTIONS 251 11.1 C D E F DOMAIN OF MAITOTOXIN 251 11.1.1 TARGET
RELEVANCE 251 11.1.2 SYNTHETIC PLANNING 253 11.1.3 SYNTHESIS 253
11.1.4 DISCUSSION 256 REFERENCES 261
|
| any_adam_object | 1 |
| author | Sierra, Miguel A. Torre, María C. de la Cossío, Fernando P. |
| author_GND | (DE-588)129516562 (DE-588)129516589 (DE-588)1035794799 |
| author_facet | Sierra, Miguel A. Torre, María C. de la Cossío, Fernando P. |
| author_role | aut aut aut |
| author_sort | Sierra, Miguel A. |
| author_variant | m a s ma mas m c d l t mcdl mcdlt f p c fp fpc |
| building | Verbundindex |
| bvnumber | BV041092565 |
| classification_rvk | VK 5500 |
| classification_tum | CHE 620f CHE 624f |
| ctrlnum | (OCoLC)852486699 (DE-599)BSZ370980859 |
| dewey-full | 547.2 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV041092565 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T00:39:25Z |
| institution | BVB |
| isbn | 9783527329762 9783527654628 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-026069133 |
| oclc_num | 852486699 |
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| owner_facet | DE-91G DE-BY-TUM DE-29T DE-20 DE-11 DE-92 |
| physical | XXI, 266 S. graph. Darst. |
| publishDate | 2013 |
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| publishDateSort | 2013 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Sierra, Miguel A. Verfasser (DE-588)129516562 aut More dead ends and detours en route to successful total synthesis Miguel A. Sierra ; María C. de la Torre, and Fernando P. Cossío Weinheim Wiley-VCH 2013 XXI, 266 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Totalsynthese (DE-588)4412308-5 gnd rswk-swf Naturstoff (DE-588)4041418-8 gnd rswk-swf Naturstoff (DE-588)4041418-8 s Totalsynthese (DE-588)4412308-5 s DE-604 Torre, María C. de la Verfasser (DE-588)129516589 aut Cossío, Fernando P. Verfasser (DE-588)1035794799 aut Erscheint auch als Online-Ausgabe, EPUB 978-3-527-65464-2 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-65463-5 Erscheint auch als Online-Ausgabe, PDF 978-3-527-65465-9 V:DE-576;X:wiley image/jpeg http://swbplus.bsz-bw.de/bsz370980859cov.htm Cover DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026069133&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Sierra, Miguel A. Torre, María C. de la Cossío, Fernando P. More dead ends and detours en route to successful total synthesis Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| subject_GND | (DE-588)4412308-5 (DE-588)4041418-8 |
| title | More dead ends and detours en route to successful total synthesis |
| title_auth | More dead ends and detours en route to successful total synthesis |
| title_exact_search | More dead ends and detours en route to successful total synthesis |
| title_full | More dead ends and detours en route to successful total synthesis Miguel A. Sierra ; María C. de la Torre, and Fernando P. Cossío |
| title_fullStr | More dead ends and detours en route to successful total synthesis Miguel A. Sierra ; María C. de la Torre, and Fernando P. Cossío |
| title_full_unstemmed | More dead ends and detours en route to successful total synthesis Miguel A. Sierra ; María C. de la Torre, and Fernando P. Cossío |
| title_short | More dead ends and detours |
| title_sort | more dead ends and detours en route to successful total synthesis |
| title_sub | en route to successful total synthesis |
| topic | Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| topic_facet | Totalsynthese Naturstoff |
| url | http://swbplus.bsz-bw.de/bsz370980859cov.htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026069133&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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