Multi-Step Organic Synthesis A Guide Through Experiments

Cover......Page 1
Title Page......Page 4
Copyright......Page 5
Dedication......Page 6
Contents......Page 8
Preface......Page 12
List of Abbreviations......Page 14
Chapter 1 Atovaquone: An Antipneumocystic Agent......Page 18
Answers......Page 21
References......Page 25
Chapter 2 SEN794: An SMO Receptor Antagonist......Page 26
Answers......Page 30
References......Page 37
3.1 Synthesis of Fragment 2......Page 38
3.2 Synthesis of Fragment 3......Page 43
3.3 Fragment Assembly and End of Synthesis......Page 44
Answers......Page 46
References......Page 57
Chapter 4 Synthesis of Eletriptan......Page 58
Answers......Page 62
References......Page 67
Chapter 5 Total Synthesis and Structure Revision of Streptophenazine A......Page 68
Answers......Page 71
References......Page 76
Chapter 6 Synthesis of Leiodermatolide, A Biologically Active Macrolide......Page 78
6.1.1 Preparation of Compound 2......Page 79
6.1.3 Preparation of Compound 12......Page 80
6.2.1 Preparation of Compound 26......Page 82
6.2.2 Preparation of Fragment D......Page 83
6.3.1 Assembly of B and Formation of A by Ring‐Closing Alkyne Metathesis......Page 84
Answers......Page 85
References......Page 93
7.1 Synthesis of Azobenzene-Thiourea Derivatives......Page 94
7.2 Investigation of Catalytic Properties......Page 99
Answers......Page 102
References......Page 109
Chapter 8 Synthesis and Properties of a Photo-activatable Mimic of Pyridoxal 5ʹ-Phosphate......Page 110
Answers......Page 116
References......Page 122
9.1 Solid-Phase Synthesis of a Putative Fluorogenic Peptide Substrate for ATG4B......Page 124
9.2 Evaluation as Fluorogenic Substrates for ATG4B......Page 125
9.3 Solution-Phase Synthesis of a Fluorogenic Substrate Analog Containing a Self-Immolating Linker......Page 128
Answers......Page 129
References......Page 135
10.1 Solution Synthesis of a Water-Soluble Cyanine Fluorophore......Page 136
10.2 Synthesis of a Water-Soluble Cyanine Fluorophore Using a Polymeric Support......Page 138
10.3 Synthesis and Evaluation of Cyanine-Based NIR Peptide Probes for Monitoring Cathepsin B Activity......Page 140
Answers......Page 146
References......Page 155
11.1 Radical Approach to the Construction of the Tricyclic Core of Stemoamide......Page 158
11.2 Formal Synthesis of (±)-Stemoamide......Page 160
11.3 Enantioselective Total Synthesis of (−)-Stemoamide......Page 162
Answers......Page 165
References......Page 175
12.1 Synthesis of the Proposed Structure of Caraphenol B......Page 176
12.2 Synthesis of the Revised Structure of Caraphenol B......Page 179
Answers......Page 181
References......Page 187
13.1 Synthesis of (+)-Muricatacin......Page 188
13.2 Synthesis of (+)-epi-Muricatacin by Enantioselective Ketone Reduction......Page 190
13.3 Synthesis of (−)-Muricatacin......Page 193
Answers......Page 195
References......Page 204
14.1 Preliminary Studies: Toward the Formation of a Model Tricyclic Compound......Page 206
14.2 Synthesis of an Advanced Intermediate......Page 209
14.3 Completion of the Synthesis......Page 211
Answers......Page 213
References......Page 220
15.1 Conformational Analysis......Page 222
15.2 Synthesis of Bicyclic Lactam Templates......Page 225
15.3 Solid Phase Peptide Synthesis......Page 228
15.4 Pharmacological Study......Page 231
Answers......Page 232
References......Page 241
16.1 First Generation Mimetics: Synthesis and Biological Evaluation......Page 244
16.2 Structural Analysis and Mechanism of Action......Page 246
16.3.1 Synthesis of Homophenylalanine (Hfe)......Page 248
16.3.2 Synthesis of Phenylglycine (Phg)......Page 249
16.3.3 Synthesis of 4‐Chlorophenylalanine (ClF)......Page 251
16.3.5 Synthesis of 1‐Naphtylalanine (1‐Nal)......Page 252
16.3.6 Synthesis of Cyclohexylalanine (Cha)......Page 253
16.3.7 Synthesis of Norleucine (Nle)......Page 254
16.3.8 Synthesis of Biphenylalanine (Bip)......Page 255
Answers......Page 257
References......Page 273
Further Reading......Page 276
Index......Page 278
EULA......Page 0