Drawing on the vast amount of experience the author has gained from working in industrial and university laboratories, this collection of excerpt reports contains essential details from literature relevant to the synthesis of compounds on a milligram to kilogram scale. The excerpts are composed using ChemDraw software and compiled in a Word document. A number of the compounds that have eluded efficient preparation in the past are now presented. Material which will improve any chemist's existing synthetic methodology can be found here. Each of the six chapters, with eighty excerpts, illustrates a novel application of syntheses selected from twenty-first-century literature. Features: This professional text describes many of the classical and contemporary methods of synthesis that have recently found great value in the preparation of needed target compounds in the required quantities. This special topic work is a description of the preparation of chemicals used in the study and development of medicinal compounds. Each of the seventy-seven excerpts are graphical outlines of sequential reactions and intermediates used to produce the synthetic targets. A wide variety of classical and modern methodologies are included in this collection. Many of the excerpts are supplemented with experimental details and mechanistic insights into the reactions involved. This user-friendly professional text provides enormous aid in designing synthetic sequences. Appeals to a broad audience in both academic and industrial laboratories, basically any chemist in need of designing a synthetic sequence or just selecting a single reaction. Author has a vast amount of experience gained from working in academic and industrial laboratories.

Introduction viii

Chapter 1 Non-Natural Organic Compounds 1

Thienodiazapinone Anticancer Agents 2

Tetraarylmethane 3

Fluorinated Liquid Crystal 5

β-Hydroxytyrosine Tripeptide 7

Aza Crown Ether: Chiral PTC Agent 10

Triple- ~13C Labeled Pyridoxine 12

Nanorod 14

Borazaphenanthrene 16

~18F-Radiotracer Roadmap 18

Technecium Radiotracer 20

Cytotoxic Ferrocene Analog 23

Epatazocine 25

Pyridine Aza Crown Hybrid Chelate 27

Chapter 2 Structural Moieties and Functional Groups 28

1,3-Diarylindene Synthesis 29

Nitriles from Terminal Alkynes 31

Thiocyanate Transformations 32

Dehydrogenative Cross Coupling 34

4-Methoxyphthalaldehyde 35

Naphthalimide 37

Glutamate Neuroantagonist 38

Phthalides 40

10-Undecylenic Acid 42

Pentafluorosulfanyl – SARM 45

Spirolactone 47

Tetrahydroquinoline (THQ) Synthesis 49

1,3,5-Triolmotif Synthon 52

Chapter 3 Natural Products 53

3-Epi Jurenolide C 54

Morphine 59

Tocopherol 61

Acremines F, A, and B 64

Altoscholarsine C and D 66

Cryptochiral I – Four Compounds 70

Cryptochiral II: Leafminer Phermone 74

Oxypalmatine 77

Galeillalactone 79

Phyllostictine 82

Karrikin 84

Mersicarpine 85

Lycoposerramine 87

Chapter 4 Diversification and Simplification 91

Two Aminophilic Reagents 92

Truncated Abyssomicin 94

Knoevenagel Adducts of Fuligocandin B 96

Core Pyrrolidinone of the Calyciphylines 98

β2,2-Disubstituted Amino Acid 100

Conformationally Constrained Epothilone 103

Kaurene Derivative 105

Conolidine Simplified 107

Annulated Thiophene 109

Modified Pyrazolaquinolinone Drug 111

The Bispiro Core of Mollanol A 113

Pregabalen 115

Sphingosine Analogs 116

Vancomycin Aminoglycal 118

Chapter 5 Name Reactions 120

Undesired Product 121

Addendum 123

Aza-Claisen Rearrangement 124

Petasis Reaction: Angular Heterospirocycle 127

Methyl Carlactonate 129

Robinson Reaction Products I, II, and III 131

NHC Catalysed Aldehyde Coupling 133

Strecker Reaction – Cyclic Aminonitriles 136

Oxy-Bridged Tetracyclic Framework 138

Achmatowicz – Decytospolide B 141

The Quaternary Center of Lyngbyatoxin A 143

Chapter 6 Variations on a Synthetic Sequence 146

Triclodic Acids 147

Heteropolycyclics 148

An Erythrina Alkaloid 154

Elemine 157

3-(R)-Hydroxyglutamic Acid 159

(R) and (S) 3-(n-Propyl)-Butyrolactone 161

Indole – Quinoline Hybrids 163

Isoquinoline Alkaloid 165

Lily-of-the-Valley Odorant 167

Enzyme Receptor Ligand 169

Altersolanols A and N 172

Teneraic Acid 175

Pachastrissamine 177

Biliruben Metabolites 180

Index 183

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