Dead ends and detours: direct ways to successful total synthesis
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2004
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Physical Description: | XIV, 276 |
| ISBN: | 3527306447 |
Staff View
MARC
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Record in the Search Index
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|---|---|
| adam_text | Contents
Foreword
.....................................................................................................................
VII
Preface
...........................................................................................................................
IX
Abbreviations
.............................................................................................................
XIII
Chapter
1
Introduction: From the Paper to the Laboratory
........................................................ 1
References
..............................................................................................................5
Chapter
2
Tuning-up, Tactical and Strategic Changes
.................................................................7
2.1
Tuning-up Reaction Conditions
..............................................................................7
2.1.1
(+)-13-Deoxytedanolide
.........................................................................................8
2.2
Tactical Changes
..................................................................................................12
2.2.1
(+)-Taxusin
...........................................................................................................13
2.2.2
(-^Strychnine
.......................................................................................................19
2.3
Strategic Changes
.................................................................................................25
2.3.1
The Core of (+)-Lepicidin AAglycon
..................................................................26
2.3.2
(±)-Scopadulin
......................................................................................................31
References
............................................................................................................39
Chapter
3
Working with Models
...................................................................................................41
3.1
(-J-Stenine
............................................................................................................41
3.2
(+)-Piperazinomycin
.............................................................................................52
3.3
(+)-Damavaricin
D
...............................................................................................55
3.4
Dynemicin A
........................................................................................................63
References
............................................................................................................72
Chapter
4
The Unexpected Reactivity or Inertia of Common Functional Groups
...................75
4.1
Pseudotabersonine
................................................................................................75
4.2
Octalactins A and
В
..............................................................................................81
4.3
(-(-Polycavernoside A
..........................................................................................88
References
............................................................................................................98
XII Contents
Chapter
5
The Influence of Remote Substituents
........................................................................99
5.1
Alive Dead Steric Volume
................................................................................99
5.1.1
(±)-Lubiminol
.....................................................................................................
10°
5.1.2
(±)-Myracin
С
....................................................................................................
107
5.2
The Reactive Remote Group
..............................................................................
H8
5.2.1
(-VChaparrinone
................................................................................................118
5.2.2
(i^Akuammicine
...............................................................................................126
5.2.3
Mylbemycin
D
....................................................................................................132
References
..........................................................................................................139
Chapter
6
The Elusive Side Chain
..............................................................................................141
6.1
(iJ-Scopadulcic Acid
В
......................................................................................141
6.2
Dysidiolide
.........................................................................................................150
6.3
(+)-Epoxydictymene
...........................................................................................156
6.4
(±)-Lepadiformine
..............................................................................................168
References
..........................................................................................................172
Chapter
7
The Unpredictable Stereochemistry
.......................................................................... 175
7.1
Nocardiones A and
В
..........................................................................................175
7.2
(±)-Breynolide
....................................................................................................179
7.3
Hamigerans A and
В
...........................................................................................192
7.4
CalphostinA
.......................................................................................................200
7.5
Fragment C3-C
10
of Cytovaricin
.......................................................................205
7.6
Goniocin
.............................................................................................................208
References
..........................................................................................................216
Chapter
8
Reluctant Ring Closures
.............................................................................................219
8.1
Discorhabdin
С
...................................................................................................219
8.2
Discorhabdin A
...................................................................................................226
8.3
Frondosin
В
........................................................................................................228
8.4
H-Laulimalide
...................................................................................................238
8.5
«/¡/-Rubifolide
.....................................................................................................246
8.6
Roseophilin Tricyclic Core: The Formal Total Synthesis of Roseophilin
..........255
8.7
(-J-Papuamine
....................................................................................................261
References
..........................................................................................................269
Subject Index
...............................................................................................................271
A plethora of publications provide valuable information for the
organic chemist, yet the results are almost always based on successful
reactions. However, a chemist s life is unfortunately not that easy.
On the contrary, trial and error is still one of the most commonly used
methods. Thus it would be useful to have access to those syntheses
that do not work, since they also provide important results of great
importance for further synthesis.
This long-awaited book by M.A. Sierra and
M.C. de la
Torre fills
just such a gap. Using major total syntheses they explain the most
varied problems and recommend ways out of such dilemmas:
Problems at the start and end of a synthesis, difficult and unexpected
reactivities of functional groups, problems due to steric properties
and much more.
The result is a true wealth of information for any organic chemist.
The essential tool for successful total synthesis.
|
| any_adam_object | 1 |
| author | Sierra, Miguel A. Torre, María C. de la |
| author_GND | (DE-588)129516562 (DE-588)129516589 |
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| author_sort | Sierra, Miguel A. |
| author_variant | m a s ma mas m c d l t mcdl mcdlt |
| building | Verbundindex |
| bvnumber | BV019626386 |
| callnumber-first | Q - Science |
| callnumber-label | QD262 |
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| callnumber-search | QD262 |
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| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 5500 VK 8500 |
| classification_tum | CHE 620f |
| ctrlnum | (OCoLC)249528002 (DE-599)BVBBV019626386 |
| 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.BV019626386 |
| illustrated | Not Illustrated |
| indexdate | 2024-07-09T20:01:38Z |
| institution | BVB |
| isbn | 3527306447 |
| language | English |
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| spelling | Sierra, Miguel A. Verfasser (DE-588)129516562 aut Dead ends and detours direct ways to successful total synthesis Miguel A. Sierra ; Maria C. de la Torre Weinheim Wiley-VCH 2004 XIV, 276 txt rdacontent n rdamedia nc rdacarrier Naturstoff - Totalsynthese Organic compounds Synthesis 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 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012955640&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012955640&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Sierra, Miguel A. Torre, María C. de la Dead ends and detours direct ways to successful total synthesis Naturstoff - Totalsynthese Organic compounds Synthesis Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| subject_GND | (DE-588)4412308-5 (DE-588)4041418-8 |
| title | Dead ends and detours direct ways to successful total synthesis |
| title_auth | Dead ends and detours direct ways to successful total synthesis |
| title_exact_search | Dead ends and detours direct ways to successful total synthesis |
| title_full | Dead ends and detours direct ways to successful total synthesis Miguel A. Sierra ; Maria C. de la Torre |
| title_fullStr | Dead ends and detours direct ways to successful total synthesis Miguel A. Sierra ; Maria C. de la Torre |
| title_full_unstemmed | Dead ends and detours direct ways to successful total synthesis Miguel A. Sierra ; Maria C. de la Torre |
| title_short | Dead ends and detours |
| title_sort | dead ends and detours direct ways to successful total synthesis |
| title_sub | direct ways to successful total synthesis |
| topic | Naturstoff - Totalsynthese Organic compounds Synthesis Totalsynthese (DE-588)4412308-5 gnd Naturstoff (DE-588)4041418-8 gnd |
| topic_facet | Naturstoff - Totalsynthese Organic compounds Synthesis Totalsynthese Naturstoff |
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