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.

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.

1;Cover;1 2;Title Page;5 3;Copyright;6 4;Dedication;7 5;Contents;9 6;Preface;13 7;List of Abbreviations;15 8;Chapter 1 Atovaquone: An Antipneumocystic Agent;19 8.1;Answers;22 8.2;References;26 9;Chapter 2 SEN794: An SMO Receptor Antagonist;27 9.1;Answers;31 9.2;References;38 10;Chapter 3 Synthesis of an H1-H3 Antagonist;39 10.1;3.1 Synthesis of Fragment 2;39 10.2;3.2 Synthesis of Fragment 3;44 10.3;3.3 Fragment Assembly and End of Synthesis;45 10.4;Answers;47 10.5;References;58 11;Chapter 4 Synthesis of Eletriptan;59 11.1;Answers;63 11.2;References;68 12;Chapter 5 Total Synthesis and Structure Revision of Streptophenazine A;69 12.1;Answers;72 12.2;References;77 13;Chapter 6 Synthesis of Leiodermatolide, A Biologically Active Macrolide;79 13.1;6.1 Access to Fragment C;80 13.1.1;6.1.1 Preparation of Compound 2;80 13.1.2;6.1.2 Preparation of Compound 7;81 13.1.3;6.1.3 Preparation of Compound 12;81 13.1.4;6.1.4 Preparation of Fragment C;83 13.2;6.2 Access to Fragment D;83 13.2.1;6.2.1 Preparation of Compound 26;83 13.2.2;6.2.2 Preparation of Fragment D;84 13.3;6.3 Final Steps;85 13.3.1;6.3.1 Assembly of B and Formation of A by Ring?Closing Alkyne Metathesis;85 13.3.2;6.3.2 Coupling of Sugar and Macrocycle;86 13.4;Answers;86 13.5;References;94 14;Chapter 7 Azobenzene-Thiourea Catalysts for the Control of Chemical Reactivity with Light;95 14.1;7.1 Synthesis of Azobenzene-Thiourea Derivatives;95 14.2;7.2 Investigation of Catalytic Properties;100 14.3;Answers;103 14.4;References;110 15;Chapter 8 Synthesis and Properties of a Photo-activatable Mimic of Pyridoxal 5?-Phosphate;111 15.1;Answers;117 15.2;References;123 16;Chapter 9 Fluorescent Peptides for Monitoring Activity of Autophagy-Initiating Enzyme;125 16.1;9.1 Solid-Phase Synthesis of a Putative Fluorogenic Peptide Substrate for ATG4B;125 16.2;9.2 Evaluation as Fluorogenic Substrates for ATG4B;126 16.3;9.3 Solution-Phase Synthesis of a Fluorogenic Substrate Analog Containing a Self-Immolating Linker;129 16.4;Answers;130 16.5;References;136 17;Chapter 10 Fluorescent Peptide Probes for Cathepsin B;137 17.1;10.1 Solution Synthesis of a Water-Soluble Cyanine Fluorophore;137 17.2;10.2 Synthesis of a Water-Soluble Cyanine Fluorophore Using a Polymeric Support;139 17.3;10.3 Synthesis and Evaluation of Cyanine-Based NIR Peptide Probes for Monitoring Cathepsin B Activity;141 17.4;Answers;147 17.5;References;156 18;Chapter 11 Total Synthesis of Stemoamide;159 18.1;11.1 Radical Approach to the Construction of the Tricyclic Core of Stemoamide;159 18.2;11.2 Formal Synthesis of (±)-Stemoamide;161 18.3;11.3 Enantioselective Total Synthesis of (?)-Stemoamide;163 18.4;Answers;166 18.5;References;176 19;Chapter 12 Total Synthesis and Structure Revision of Caraphenol B;177 19.1;12.1 Synthesis of the Proposed Structure of Caraphenol B;177 19.2;12.2 Synthesis of the Revised Structure of Caraphenol B;180 19.3;Answers;182 19.4;References;188 20;Chapter 13 Synthetic Routes Toward Muricatacin and Analogs;189 20.1;13.1 Synthesis of (+)-Muricatacin;189 20.2;13.2 Synthesis of (+)-epi-Muricatacin by Enantioselective Ketone Reduction;191 20.3;13.3 Synthesis of (?)-Muricatacin;194 20.4;Answers;196 20.5;References;205 21;Chapter 14 Asymmetric Synthesis of (?)-Martinellic Acid;207 21.1;14.1 Preliminary Studies: Toward the Formation of a Model Tricyclic Compound;207 21.2;14.2 Synthesis of an Advanced Intermediate;210 21.3;14.3 Completion of the Synthesis;212 21.4;Answers;214 21.5;References;221 22;Chapter 15 Cyclic Pseudopeptides as Potent Integrin Antagonists;223 22.1;15.1 Conformational Analysis;223 22.2;15.2 Synthesis of Bicyclic Lactam Templates;226 22.3;15.3 Solid Phase Peptide Synthesis;229 22.4;15.4 Pharmacological Study;232 22.5;Answers;233 22.6;References;242 23;Chapter 16 Enantioselective Synthesis of Nonnatural Amino Acids for Incorporation in Antimicrobial Peptides;245 23.1;16.1 First Generation Mimetics: Synthesis and Biological Evaluation;245 23.2;16.2 Structural Analysis and Mechanism of Action;247