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Multi-Step Organic Synthesis: A Guide Through Experiments

ISBN: 978-3-527-69899-8
350 pages
August 2017
Multi-Step Organic Synthesis: A Guide Through Experiments (352769899X) cover image


Combining theoretical knowledge of synthetic transformations, practical considerations, structural elucidation by interpretation of spectroscopic data as well as rationalization of structure-property relations, this textbook presents a series of 16 independent exercises, including detailed descriptions of experimental procedures, questions, and answers. The experimental descriptions are very helpful for guiding less experienced students towards a better understanding of practical aspects in synthetic organic chemistry, while the broad scope of the questions and answers is excellent for learning purposes. The exercises are based on published research articles, adapted for didactic purposes, and will thus inspire students by way of having to solve real-life problems in chemistry.
A must-have for MSc and PhD students as well as postdocs in organic chemistry and related disciplines, and lecturers and organizers of lab courses in organic chemistry.
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Table of Contents

Preface xi

List of Abbreviations xiii

1 Atovaquone: An Antipneumocystic Agent 1

Answers 4

References 8

2 SEN794: An SMO Receptor Antagonist 9

Answers 13

References 20

3 Synthesis of an H1–H3 Antagonist 21

3.1 Synthesis of Fragment 2 21

3.2 Synthesis of Fragment 3 26

3.3 Fragment Assembly and End of Synthesis 27

Answers 29

References 40

4 Synthesis of Eletriptan 41

Answers 45

References 50

5 Total Synthesis and Structure Revision of Streptophenazine A 51 Answers 54

References 59

6 Synthesis of Leiodermatolide, A Biologically Active Macrolide 61

6.1 Access to Fragment C 62

6.1.1 Preparation of Compound 2 62

6.1.2 Preparation of Compound 7 63

6.1.3 Preparation of Compound 12 63

6.1.4 Preparation of Fragment C 65

6.2 Access to Fragment D 65

6.2.1 Preparation of Compound 26 65

6.2.2 Preparation of Fragment D 66

6.3 Final Steps 67

6.3.1 Assembly of B and Formation of A by Ring?]Closing Alkyne Metathesis 67

6.3.2 Coupling of Sugar and Macrocycle 68

Answers 68

References 76

7 Azobenzene-Thiourea Catalysts for the Control of Chemical Reactivity with Light 77

7.1 Synthesis of Azobenzene-Thiourea Derivatives 77

7.2 Investigation of Catalytic Properties 82

Answers 85

References 92

8 Synthesis and Properties of a Photo-activatable Mimic of Pyridoxal 5ʹ-Phosphate 93

Answers 99

References 105

9 Fluorescent Peptides for Monitoring Activity of Autophagy-Initiating Enzyme 107

9.1 Solid-Phase Synthesis of a Putative Fluorogenic Peptide Substrate for ATG4B 107

9.2 Evaluation as Fluorogenic Substrates for ATG4B 108

9.3 Solution-Phase Synthesis of a Fluorogenic Substrate Analog Containing a Self-Immolating Linker 111

Answers 112

References 118

10 Fluorescent Peptide Probes for Cathepsin B 119

10.1 Solution Synthesis of a Water-Soluble Cyanine Fluorophore 119

10.2 Synthesis of a Water-Soluble Cyanine Fluorophore Using a Polymeric Support 121

10.3 Synthesis and Evaluation of Cyanine-Based NIR Peptide Probes for Monitoring Cathepsin B Activity 123

Answers 129

References 138

11 Total Synthesis of Stemoamide 141

11.1 Radical Approach to the Construction of the Tricyclic Core of Stemoamide 141

11.2 Formal Synthesis of (})-Stemoamide 143

11.3 Enantioselective Total Synthesis of (−)-Stemoamide 145

Answers 148

References 158

12 Total Synthesis and Structure Revision of Caraphenol B 159

12.1 Synthesis of the Proposed Structure of Caraphenol B 159

12.2 Synthesis of the Revised Structure of Caraphenol B 162

Answers 164

References 170

13 Synthetic Routes Toward Muricatacin and Analogs 171

13.1 Synthesis of (+)-Muricatacin 171

13.2 Synthesis of (+)-epi-Muricatacin by Enantioselective Ketone

Reduction 173

13.3 Synthesis of (−)-Muricatacin 176

Answers 178

References 187

14 Asymmetric Synthesis of (−)-Martinellic Acid 189

14.1 Preliminary Studies: Toward the Formation of a Model Tricyclic Compound 189

14.2 Synthesis of an Advanced Intermediate 192

14.3 Completion of the Synthesis 194

Answers 196

References 203

15 Cyclic Pseudopeptides as Potent Integrin Antagonists 205

15.1 Conformational Analysis 205

15.2 Synthesis of Bicyclic Lactam Templates 208

15.3 Solid Phase Peptide Synthesis 211

15.4 Pharmacological Study 214

Answers 215

References 224

16 Enantioselective Synthesis of Nonnatural Amino Acids for Incorporation in Antimicrobial Peptides 227

16.1 First Generation Mimetics: Synthesis and Biological Evaluation 227

16.2 Structural Analysis and Mechanism of Action 229

16.3 Sequence Optimization: Synthesis of Nonnatural Amino Acids 231

16.3.1 Synthesis of Homophenylalanine (Hfe) 231

16.3.2 Synthesis of Phenylglycine (Phg) 232

16.3.3 Synthesis of 4?]Chlorophenylalanine (ClF) 234

16.3.4 Synthesis of 2?]Naphtylalanine (2?]Nal) 235

16.3.5 Synthesis of 1?]Naphtylalanine (1?]Nal) 235

16.3.6 Synthesis of Cyclohexylalanine (Cha) 236

16.3.7 Synthesis of Norleucine (Nle) 237

16.3.8 Synthesis of Biphenylalanine (Bip) 238

Answers 240

References 256

Further Reading 259

Index 261

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Author Information

Nicolas Bogliotti is Assistant Professor at Ecole normale superieure Paris-Saclay, France. After his undergraduate studies at Universite Nice Sophia-Antipolis, France, he obtained his MSc and PhD Degrees at Universite Pierre et Marie Curie in Paris, France. He was a postdoc at ETH Zurich, Switzerland and Institut Curie, France, before his current position. His research interests focus on the synthesis of photosensitive molecules allowing visualization of recognition events, induction of a biological response and modulation of chemical reactivity.

Roba Moumne is Assistant Professor at Universite Pierre et Marie Curie, France. She studied chemistry and completed her MSc and PhD at the same university. Before her current position, she was also a postdoctoral fellow at Max-Planck-Institut in Mulheim and der Ruhr, Germany, at University of Zurich, Switzerland and at Universite Paris Descartes, France. Her research interests include bioorganic chemistry and peptide synthesis.
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