Protecting-Group-Free Organic Synthesis

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 synthesis" and back the global need of practicing green chemistry. The only resource of its kind to focus entirely on protecting-group-free synthesis, it is edited by a leading practitioner in the field, and features enlightening contributions by top experts and researchers from across the globe.

The introductory chapter includes a concise review of historical developments, and discusses the concepts, need for, and future prospects of protecting-group-free synthesis. Following this, the book presents 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 derivatives, glycol-polymers and glyco-conjugates. The book concludes with a chapter on latent functionality as a tactic toward formal 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 because it renders syntheses more economical

Protecting-Group-Free Organic Synthesis: Improving Economy and Efficiency is an important book for academic researchers in synthetic organic chemistry, green chemistry, medicinal and pharmaceutical chemistry, biochemistry, and drug discovery.

Auteur

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).

Contenu
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-Diepi-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-1 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

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 Kadota

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)-Alstoscholarines 72

3.11 Berkelic Acid 73

3.12 Myxalamide A 74

3.13 Pipercyclobutanamide A 76

3.14 Fusarisetin A 78

3.15 Rhazinilam 78

3.16 Yezo'otogirin C 81

3.17 Clavosolide A 81

3.18 Conclusion 84

References 84

4 Protecting-Group-Free Synthesis of Natural Products and Analogs, Part III 87
Alakesh 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 Aggarwal 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...