Protecting-group-free organic synthesis: improving economy and efficiency
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| Format: | Book |
| Language: | English |
| Published: |
Hoboken, NJ, USA ; Chichester, West Sussex, UK
Wiley
[2018]l
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Physical Description: | xviii, 265 Seiten Illustrationen |
| ISBN: | 9781119295204 |
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Record in the Search Index
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| adam_text | Contents
List of Contributors xi
Foreword by Prof. W. Hoffmann xiii
Foreword by Prof. G. Mehta xv
Preface xvii
1 Introduction: Concepts, History, Need, and Future Prospects of
Protecting-Group-Free Synthesis 1
Rodney A. Fernandes
1.1 Introduction, Concepts, and Brief History 1
1.2 Need and Future Prospects of Protecting-Group-Free Synthesis 7
References 8
2 Protecting-Group-Free Synthesis of Natural Products and Analogs, Part I 11
Rodney A. Fernandes
2.1 Introduction 11
2.2 Mytilipin A 12
2.3 Chokols 13
2.4 (±)-Diospongin A 14
2.5 (-)-Bitungolide F 15
2.6 (+)-Brevisamide 16
2.7 21,22-Z ie/?i-membrarolin 17
2.8 (±)-Pogostol and (±)-Kessane 18
2.9 (+)-Allopumiliotoxin 267A 19
2.10 (-)-Hortonones A-C 19
2.11 (-)-Heliophenanthrone 21
2.12 (-)-Pycnanthuquinone C 21
2.13 (+)-Aplykurodinone-l 22
2.14 (±)-Hippolachnin A 23
2.15 (+)-Linoxepin 25
2.16 (+)-Antofine and (-)-Cryptopleurine 26
2.17 (+)-Tylophorine 28
2.18 (±)-Cruciferane 30
2.19 (+)-Artemisinin 31
2.20 (±)-Dievodiamine 32
viii
Contents
2.21 (-)-Chaetominine 33
2.22 Rubicordifolin 34
2.23 (+)-Caribenol A 35
2.24 Camptothecin and 10-Hydroxycamptothecin 35
2.25 (+)-Ainsliadimer A 37
2.26 Cannabicyclol, Clusiacyclols A and B, Iso-Eriobrucinols A and B,
and Eriobrucinol 37
2.27 (-)-Mersicarpine, (-)-Scholarisine G, (+)-Melodinine,
(-)-Leuconoxine, and (-)-Leuconolam 38
2.28 (-)-Lannotinidine B 40
2.29 (-)-Lycopodine 41
2.30 (-)-Lycospidine A 42
2.31 Transtaganolides C and D 43
2.32 (+)-Chatancin 44
2.33 (-)-Jiadifenolide 45
2.34 Pallambins C and D 46
2.35 (+)-Vellosimine 46
2.36 (-)-Pallavicinin and (+) Neopallavicinin 47
2.37 Asteriscunolides A-D and Asteriscanolide 49
2.38 (-)- and (+)-Palmyrolide A 50
2.39 (±)-Bipinnatin J 51
2.40 Cyanolide 52
2.41 Conclusions 53
References 55
3 Protecting-Group-Free Synthesis of Natural Products and Analogs, Part II 59
Hiroyoshi Takamura and Isao Kodota
3.1 Introduction 59
3.2 Hapalindole U and Ambiguine H 60
3.3 Stenine 61
3.4 Neostenine 63
3.5 Englerin A 64
3.6 Shimalactones A and B 66
3.7 Cyanthiwigin F 66
3.8 Sintokamides A, B, and E 69
3.9 Ecklonialactones A and B 69
3.10 (E)- and (Z)-AIstoscholarines 72
3.11 BerkelicAcid 73
3.12 Myxalamide A 74
3.13 Pipercyclobutanamide A 76
3.14 FusarisetinA 78
3.15 Rhazinilam 78
3.16 Yezobtogirin C 81
3.17 ClavosolideA 81
3.18 Conclusion 84
References 84
Contents
ix
4 Protecting-Group-Free Synthesis of Natural Products and Analogs, Part III 87
Alokesh Bisai and Vishnumaya Bisai
4.1 Introduction 87
4.2 Syntheses of Naturally Occurring Alkaloids 88
4.3 Syntheses of Naturally Occurring Terpenoids 105
4.4 Conclusions 124
References 125
5 Protecting-Group-Free Synthesis of Heterocycles 133
Trapti Aggarwaf and Akhilesh K. Verma
5.1 Introduction 133
5.2 Historical Background of Protection-Free Strategy 134
5.3 Protecting-Group-Free (PGF) Strategy for the Synthesis
of N-Heterocycles 135
5.3.1 Carbazole Substituted Compounds Using PGF Strategy 135
5.3.2 Protection-Free Synthesis of Indole-Substituted Compounds 139
5.3.3 Synthesis of Pyrrole Analogs Using Protecting-Group-Free Strategy 140
5.4 Protection-Free Synthesis of Quinoline Derivatives 142
5.5 Synthesis of Piperidine-Containing Heterocycles Without Using Protecting
Groups 143
5.6 Synthesis of Quinazolines Without Using Protecting Groups 144
5.7 Protection-Free Synthesis of Pyrrolizine Alkaloid (-)-Rosmarinecine 145
5.8 Protecting-Group-Free Synthesis of O-Heterocycles 145
5.9 Protecting-Group-Free Synthesis of N,S-Heterocycles 148
5.10 Protection-Free Synthesis of Macrocyclic Ring Heterocycles 149
5.11 Protection-Free Synthesis of Thiophene Polymer 150
5.12 Protection-Free Synthesis of Azaborine 150
5.13 Conclusion 151
References 151
6 Protecting-Group-Free Synthesis of Drugs and Pharmaceuticals 155
Remya Ramesh, Swapnif Sonawane, D. Srinivasa Reddy and Rakeshwar Bandichhor
6.1 Introduction 155
6.2 Raltegravir 158
6.3 Levetiracetam 160
6.4 Sitagliptin 163
6.4.1 Medicinal Chemistry Route 164
6.4.2 Process Chemistry Route 166
6.4.3 Greener Approach 167
6.5 Paroxetine 168
6.5.1 Medicinal Chemistry Route 168
6.5.2 Process Chemistry Route 170
6.5.3 Greener Approach 170
6.6 Synthesis of PI3I /mTOR Inhibitor Apitolisib 171
6.7 Azepinomycin 174
6.8 One-Pot Synthesis of Sulfanyl-histidine 175
X
Contents
6.9 Synthesis of an Antiwrinkle Venom Analog 175
6.10 Preparation of 5-Arylidene Rhodanine and 2,4-Thiazolidinediones 176
6.11 Se-Adenosyl-L-Selenomethionine and Analogs 177
6.12 Conclusions 178
Acknowledgment 179
References 179
7 Protecting-Group-Free Synthesis in Carbohydrate Chemistry 183
Alejandro Cordero-Vargas and Fernando Sartillo-Piscil
7.1 Introduction 183
7.2 Protecting-Group-Free Total Synthesis (PGF-TS) 184
7.3 Selective PGF Functionalization at the Anomeric Position (O-, N-,
and C-Glycosylation) 189
7.4 Selective PGF Functionalization at the Anomeric and
Nonanomeric Positions (Oxidations) 196
7.5 Conclusion 197
References 198
8 Protecting-Group-Free Synthesis of Glycosyl Derivatives, Glycopolymers,
and Glycoconjugates 201
Tomonari Tanaka
8.1 Introduction 201
8.2 Protecting-Group-Free Synthesis of Glycosyl Derivatives from Free
Saccharides 202
8.3 Protecting-Group-Free Synthesis of Glycopolymers 214
8.4 Protecting-Group-Free Synthesis of Glycoconjugates 219
8.5 Conclusions 223
References 225
9 Latent Functionality: A Tactic Toward Formal Protecting-Group-Free
Synthesis 229
Rodney A. Fernandes
9.1 Introduction 229
9.2 Latent Functionality for Direct Conversions Using Short-Term
Latent Groups 230
9.3 Silicon-Centered Latent Functionalities 235
9.4 Latent Functionality in Total Synthesis
(Long-Term Latent Groups) 240
9.5 Symmetry-Based Latent Functionality Considerations 248
9.6 Conclusions 254
References 255
Index 259
Presents a comprehensive account of established protecting-group-free
synthetic routes to molecules of medium to high complexity
This book supports synthetic chemists in
the design of strategies, which avoid or
minimize the use of protecting groups so as
to come closer to achieving an ideal synthe-
sis and back the global need of practicing
green chemistry. The only resource of its kind
to focus entirely on protecting-group-free syn-
thesis, it is edited by a leading practitioner
in the field, and features enlightening contri-
butions by top experts and researchers from
across the globe.
The introductory chapter includes a con-
cise review of historical developments,
and discusses the concepts, need for, and
future prospects of protecting-group-free
synthesis. Following this, the book pres-
ents information on protecting-group-free
synthesis of complex natural products and
analogues, heterocycles, drugs, and related
pharmaceuticals. Later chapters discuss
practicing protecting-group-free synthesis
using carbohydrates and of glycosyl deriva-
tives, glycolpolymers and glyco-conjugates.
The book concludes with a chapter on
latent functionality as a tactic toward for-
mal protecting-group-free synthesis.
• A comprehensive account of established
protecting-group-free (PGF) synthetic routes
to molecules of medium to high complexity
• Benefits total synthesis, methodology
development and drug synthesis researchers
• Supports synthetic chemists in the design
of strategies, which avoid or minimize the
use of protecting groups so as to come
closer to achieving an ideal synthesis
and support the global need of practicing
green chemistry
• Covers a topic that is gaining importance be-
cause it renders syntheses more economical
Protecting-Group-Free Organic Synthesis:
Improving Economy and Efficiency is an im-
portant book for academic researchers in
synthetic organic chemistry, green chemistry,
medicinal and pharmaceutical chemistry,
biochemistry, and drug discovery.
Rodney A. Fernandes, PhD, is a Professor in the Department of
Chemistry at the Indian Institute of Technology Bombay, Mumbai,
India. He is a practitioner of total synthesis, asymmetric synthesis, and
the development of new methodologies with a special emphasis on
protecting-group-free synthesis. Many well-known syntheses have
been significantly modified in his laboratory by designing protecting-
group-free strategies enabling a good level of step-economy. He has
89 publications (including 6 review articles) and 8 patents. He was
the recipient of the Indian National Science Academy (INSA) Young
Scientists Medal Award in 2004 and is elected Fellow of Maharashtra
Academy of Sciences (2015).
Cover Design: Wiley
Cover Image: © Aleksandr Simonov/Shutterstock
www.wiley.com
Wiley ir-rr
ISBN 978-1-119-29520-4
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| spelling | Protecting-group-free organic synthesis improving economy and efficiency edited by Rodney A. Fernandes (Indian Institute of Technology Bombay, Mumbay, India) Hoboken, NJ, USA ; Chichester, West Sussex, UK Wiley [2018]l © 2018 xviii, 265 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s DE-604 Fernandes, Rodney A. (DE-588)1165235811 edt Erscheint auch als Online-Ausgabe, PDF 978-1-119-29519-8 Erscheint auch als Online-Ausgabe, EPUB 978-1-119-29522-8 Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030326615&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030326615&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Protecting-group-free organic synthesis improving economy and efficiency Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4075695-6 |
| title | Protecting-group-free organic synthesis improving economy and efficiency |
| title_auth | Protecting-group-free organic synthesis improving economy and efficiency |
| title_exact_search | Protecting-group-free organic synthesis improving economy and efficiency |
| title_full | Protecting-group-free organic synthesis improving economy and efficiency edited by Rodney A. Fernandes (Indian Institute of Technology Bombay, Mumbay, India) |
| title_fullStr | Protecting-group-free organic synthesis improving economy and efficiency edited by Rodney A. Fernandes (Indian Institute of Technology Bombay, Mumbay, India) |
| title_full_unstemmed | Protecting-group-free organic synthesis improving economy and efficiency edited by Rodney A. Fernandes (Indian Institute of Technology Bombay, Mumbay, India) |
| title_short | Protecting-group-free organic synthesis |
| title_sort | protecting group free organic synthesis improving economy and efficiency |
| title_sub | improving economy and efficiency |
| topic | Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Organic compounds Synthesis Organische Synthese |
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