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More Dead Ends and Detours. En Route to Successful Total Synthesis - Product Image

More Dead Ends and Detours. En Route to Successful Total Synthesis

  • Published: May 2013
  • Region: Global
  • 288 Pages
  • John Wiley and Sons Ltd

Success comes in many forms and in synthesis it can be a failure that results in their ultimate successful solutions. This long-awaited sequel to "Dead Ends and Detours" retains the proven concept while featuring over 20 new case studies of failed strategies and their (successful) solutions in natural product total synthesis. Additionally, computational models are used to discuss the problem in much more detail and to provide readers with additional information not found in the primary literature. The topics range from classic synthetic reactions (e.g. Diels Alder reaction), metal-mediated coupling reactions, metathesis, and asymmetric catalysis to the importance of protecting and activating groups.

This book will benefit not only graduate students in organic chemistry but also advanced researchers as they gain knowledge derived from the step-by-step analysis of mistakes made in the past and, thus be able to improve their own chemical reaction planning. With its coverage of the most commonly applied reaction types, the book perfectly complements its predecessor, which focuses on general aspects, such as reactivity and selectivity.

Foreword XIII

Preface XVII

Abbreviations and Acronyms XIX

1 Introduction 1

1.1 Intermediate in the Total Synthesis of Brevetoxin A 3

1.1.1 Target Relevance 4

1.1.2 Synthetic Planning for Brevetoxin A (1.1) 4

1.1.3 Synthetic Planning of Aldehyde 1.4 5

1.1.4 Predictable Problems 5

1.1.5 Synthesis of 1.4 5

1.1.6 Discussion 8

References 12

2 The Inertia of Conventional Functional Groups 15

2.1 Welwitindolinone A Isonitrile 15

2.1.1 Target Relevance 16

2.1.2 Synthetic Planning 16

2.1.3 Predictable Problems 16

2.1.4 Synthesis 17

2.1.5 Discussion 24

2.2 ‘‘Overprotecting-Maverick’’ Protecting Groups 26

2.2.1 Iejimalides A–D 27

2.2.2 Target Relevance 27

2.2.3 Synthetic Planning 27

2.2.4 Predictable Problems 28

2.2.5 Synthesis 29

2.2.6 Discussion 35

References 37

3 The Diels–Alder Reaction 39

3.1 (-)-Platensimycin 40

3.1.1 Target Relevance 40

3.1.2 Synthetic Planning for (-)-Platinsimycin (3.1) 40

3.1.3 Predictable Problems 40

3.1.4 Discussion 46

3.2 Stephacidins A and B 49

3.2.1 Target Relevance 49

3.2.2 Synthetic Planning for ent-Stephacidins A and B 50

3.2.3 Predictable Problems 50

3.2.4 Synthesis 51

3.2.5 Discussion 54

References 58

4 The Aldol Condensation 61

4.1 The ABC Ring Moiety of (-)-Norzoanthamine 62

4.1.1 Target Relevance 62

4.1.2 Synthetic Planning for (-)-Norzoanthamine (4.1) 62

4.1.3 Predictable Problems 63

4.1.4 Synthesis 63

4.1.5 Discussion 68

4.2 (+)-TMC-151C 71

4.2.1 Target Relevance 71

4.2.2 Synthetic Planning for (+)-TMC-151C (4.30) 72

4.2.3 Synthesis 73

4.2.4 Discussion 75

References 80

5 Cyclizations: Concerted, Radical, or Polar? 83

5.1 (±)-Merrilactone A 85

5.1.1 Target Relevance 85

5.1.2 Synthetic Planning 85

5.1.3 Predictable Problems 86

5.1.4 Synthesis 86

5.1.5 Discussion 89

5.2 (-)-Pseudolaric Acid B 92

5.2.1 Target Relevance 93

5.2.2 Synthetic Planning 93

5.2.3 Predictable Problems 94

5.2.4 Synthesis 94

5.2.5 Discussion 102

5.3 Formal Synthesis of Platensimycin 104

5.3.1 Target Relevance 104

5.3.2 Synthetic Planning 104

5.3.3 Predictable Problems 105

5.3.4 Synthesis 105

5.3.5 Discussion 107

References 110

6 Macrocycles: from Reluctant Ring Closure to Reluctant Ring Opening 113

6.1 Ustiloxin D 114

6.1.1 Target Relevance 114

6.1.2 Synthetic Planning for Ustiloxin D 115

6.1.3 Predictable Problems 115

6.1.4 Synthesis of Ustiloxin D 116

6.1.5 Discussion 118

6.2 Largazole 123

6.2.1 Target Relevance 123

6.2.2 Synthetic Planning for Largazole (6.36) 123

6.2.3 Predictable Problems 124

6.2.4 Synthesis of Largazole (6.36) 125

6.2.5 Discussion 129

6.2.6 Key Synthetic Reaction 133

References 134

7 Stereochemistry, Controlled or Uncontrolled? 137

7.1 (-)-Samaderin Y 138

7.1.1 Target Relevance 138

7.1.2 Synthetic Planning 139

7.1.3 Predictable Problems 139

7.1.4 Synthesis 139

7.1.5 Discussion 145

7.2 (±)-Lyconadin A 148

7.2.1 Target Relevance 148

7.2.2 Synthetic Planning 148

7.2.3 Predictable Problems 149

7.2.4 Synthesis 149

7.2.5 Discussion 152

7.3 Vannusal B 154

7.3.1 Target Relevance 154

7.3.2 Synthetic Planning for the Originally Assigned Structure of Vannusal B (7.58) 155

7.3.3 Predictable Problems 156

7.3.4 Synthesis of the Originally Assigned Structure of Vannusal B (7.58) 156

7.3.5 Synthesis of Vannusal B (7.56) 159

7.3.6 Discussion 161

References 166

8 Transition Metal-Mediated Transformations vs "Conventional" Reactions 169

8.1 Blumiolide C 170

8.1.1 Target Relevance 171

8.1.2 Synthetic Planning for Blumiolide C (8.1) 171

8.1.3 Synthesis 171

8.1.4 Discussion 174

8.2 Arylomycin A2 179

8.2.1 Target Relevance 179

8.2.2 Synthetic Planning 180

8.2.3 Predictable Problems 180

8.2.4 Synthesis 180

8.2.5 Discussion 184

8.3 (-)-Strychnine 189

8.3.1 Target Relevance 189

8.3.2 Synthetic Planning 190

8.3.3 Predictable Problems 190

8.3.4 Synthesis of (-)-Strychnine 191

8.3.5 Discussion 195

References 198

9 When Metathesis Fails 201

9.1 (+)-Saxitoxin 202

9.1.1 Target Relevance 202

9.1.2 Synthetic Planning 203

9.1.3 Predictable Problems 204

9.1.4 Synthesis of (+)-Saxitoxin 204

9.1.5 Discussion 208

9.2 Laulimalide Family 211

9.2.1 Target Relevance 211

9.2.2 Synthetic Planning 213

9.2.3 Synthesis 214

9.2.4 Discussion 219

References 222

10 Oxidations in C–C Bond Building 225

10.1 Cortistatins A and J 226

10.1.1 Target Relevance 226

10.1.2 Synthetic Planning for Cortistatins A (10.1) and J (10.2) 226

10.1.3 Predictable Problems 227

10.1.4 Synthesis 227

10.1.5 Discussion 232

10.2 Gambierol ABC Moiety 236

10.2.1 Target Relevance 236

10.2.2 Synthetic Planning 236

10.2.3 Predictable Problems 238

10.2.4 Synthesis 238

10.2.5 Discussion 243

References 248

11 The Failure of Epoxide Ring Opening and the Limits of Cascade Reactions 251

11.1 CDEF Domain of Maitotoxin 251

11.1.1 Target Relevance 251

11.1.2 Synthetic Planning 253

11.1.3 Synthesis 253

11.1.4 Discussion 256

References 261

“Like its predecessor, this book will interest advanced, research-oriented students, their mentors, and organic synthesis practitioners.  Summing Up: Recommended.  Upper-division undergraduates through professionals/practitioners.”  (Choice, 1 January 2014)

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