Preface ........................................................ ix
1. Transition metal-mediated reactions in organic synthesis .... 1
2. Biotransformations in organic synthesis ..................... 2
3. Catalytic Enantioselective Synthesis ........................ 4
4. Enantioselective Synthesis of Borrelidin .................... 6
5. Enantioselective Ring Construction .......................... 8
6. New Routes to Heterocycles ................................. 10
7. Total Synthesis of the Galbulimima Alkaloid GB 13 .......... 12
8. Total Synthesis of Ingenol ................................. 14
9. Best Synthetic Methods: Functional Group Transformations ... 16
10. New Methods for Carbon-Carbon Bond Formation ............... 18
11. Mini-Review: Organic Reactions in Ionic Liquids ............ 20
12. Adventures in Polycyclic Ring Construction ................. 22
13. Synthesis of the Mesotricyclic Diterpenoids
Jatrophatrione and Citlalitrione ........................... 24
14. Best Synthetic Methods: Functional Group Transformations ... 26
15. The Grubbs Reaction in Organic Synthesis ................... 28
16. C-N Ring-Forming Reactions by Transition Metal-Catalyzed
Intramolecular Alkene Hydroamination ....................... 30
17. Synthesis of (+)-Phomactin A ............................... 32
18. Enzymes in Organic Synthesis ............................... 34
19. Adventures in Polycarbocyclic Construction ................. 36
20. Construction of Enantiomerically-Pure Heterocycles ......... 38
21. Best Synthetic Methods: Functional Group Transformations ... 40
22. Synthesis of (+)-4,5-Deoxyneodolabelline ................... 42
23. New Methods for Carbon-Carbon Bond Formation ............... 44
24. Strategies for Enantioselective Synthesis .................. 46
25. Preparation of Cyclic Amines ............................... 48
26. Enantioselective Total Synthesis of (+)-Amphidinolide Tl ... 50
27. Stereocontrolled Construction of Carbacycles ............... 52
28. "Organometallic" Coupling without the Metal! ............... 54
29. Preparation of Enantiomerically-Pure Building Blocks ....... 56
30. Synthesis of (-)-Strychnine ................................ 58
31. Pd-Mediated Coupling in Organic Synthesis: Recent
Milestones ................................................. 60
32. Enantioselective C-C Bond Construction: Part One of
Three ...................................................... 62
33. Enantioselective C-C Bond Construction: Part Two of
Three ...................................................... 64
34. Enantioselective C-C Bond Construction: Part Three of
Three ...................................................... 66
35. Synthesis of (-)-Podophyllotoxin ........................... 68
36. The Grubbs Reaction in Organic Synthesis: Part One of
Three ...................................................... 70
37. The Grubbs Reaction in Organic Synthesis: Part Two of
Three ...................................................... 72
38. The Grubbs Reaction in Organic Synthesis: Part Three of
Three ...................................................... 74
39. Synthesis of Deacetoxyalcyonin Acetate ..................... 76
40. Enantioselective Ring Construction: Part One of Two ........ 78
41. Enantioselective Ring Construction: Part Two of Two ........ 80
42. Alkyne Metathesis in Synthesis: Syntheses of (+)-
Ferrugine and Anatoxin-α ................................... 82
43. Catalytic Asymmetric Synthesis of Quinine and Quinidine .... 84
44. Best Synthetic Methods: Oxidation and Reduction ............ 86
45. Best Synthetic Methods: Enantioselective Oxidation and
Reduction .................................................. 88
46. Asymmetric Nucleophilic Epoxidation ........................ 90
47. Asymmetric Synthesis of Nitrogen Heterocycles .............. 92
48. Synthesis of Amphidinolide T1 .............................. 94
49. Enantioselective C-C Bond Construction: Part One of Two .... 96
50. Enantioselective C-C Bond Construction: Part Two of Two .... 98
51. Advances in Nitrogen Protection and Deprotection .......... 100
52. Enantioselective Synthesis of (+)-Tricycloclavulone ....... 102
53. Best Methods for C-C Bond Construction: Part One of
Three ..................................................... 104
54. Best Methods for C-C Bond Construction: Part Two of
Three ..................................................... 106
55. Best Methods for C-C Bond Construction: Part Three of
Three ..................................................... 108
56. Formation of Aromatic-Amino and Aromatic-Carbon Bonds ..... 110
57. Synthesis of the Dendrobatid Alkaloid 251F ................ 112
58. Enantioselective Construction of Aldol Products: Part
One of Two ................................................ 114
59. Enantioselective Construction of Aldol Products: Part
Two of Two ................................................ 116
60. Enantioselective α-Functionalization of Carbonyl
Compounds ................................................. 118
61. Synthesis of (-)-Hamigeran В .............................. 120
62. Catalytic C-C Bond-Forming Reactions ...................... 122
63. Rare Sugars are now Readily Available Chiral Pool
Starting Materials ........................................ 124
64. Alkyne Metathesis in Organic Synthesis .................... 126
65. Total Synthesis of (+-)-Sordaricin ......................... 128
66. Ru-Mediated Intramolecular Alkene Metathesis: Improved
Substrate and Catalyst Design ............................. 130
67. Heterocycle Construction by Grubbs Metathesis ............. 132
68. Natural Product Synthesis using Grubbs Metathesis:
Lasubine II, Ingenol, and Ophirin В ....................... 134
69. Synthesis of (-)-Tetrodotoxin ............................. 136
70. Diastereoselective and Enantioselective Construction
of Aza-Heterocycles ....................................... 138
71. Diastereoselective and Enantioselective Construction of
Cyclic Ethers ............................................. 140
72. Synthesis of Heterocyclic Natural Products: (-)-
Ephedradine A, (-)-α-Tocopherol, (-)-Lepadin D and
(-)-Phenserine ............................................ 142
73. Protection of N- and O-Functional Groups .................. 144
74. Synthesis of (-)-Norzoanthamine ........................... 146
75. Best Synthetic Methods: C-C Bond Formation ................ 148
76. Enantioselective Construction of Single Stereogenic
Centers ................................................... 150
77. Enantioselective Construction of Arrays of Stereogenic
Centers ................................................... 152
78. Synthesis of (-)-Brasilenyne .............................. 154
79. Best Synthetic Methods: Functional Group
Transformations ........................................... 156
80. Enantioselective Construction of Oxygenated and
Halogenated Secondary Centers ............................. 158
81. Enantioselective Construction of Aminated Secondary
Centers ................................................... 160
82. Enantioselective Synthesis of the Polyene Antibiotic
Aglycone Rimocidinolide Methyl Ester ...................... 162
83. Enantioselective Transformations of Prochiral Rings ....... 164
84. Michael Reactions for Enantioselective Ring
Construction .............................................. 166
85. Enantioselective Ring Construction by Intramolecular
C-H Insertion and by Cycloaddition ........................ 168
86. Best Synthetic Methods: Construction of Aromatic and
Heteroaromatic Rings ...................................... 170
87. Enantioselective Synthesis of (+)-Epoxomycin .............. 172
88. Best Synthetic Methods: Functionalization of Aromatic
and Heteroaromatic Rings .................................. 174
89. Best Synthetic Methods: Oxidation ......................... 176
90. Enantioselective Allylic Carbon-Carbon Bond
Construction .............................................. 178
91. Synthesis of (+)-Cyanthawigin U ........................... 180
92. Catalysts and Strategies for Alkene Metathesis ............ 182
93. N-Heterocycle Construction by Alkene Metathesis ........... 184
94. O-Heterocyclic Construction by Alkene Metathesis .......... 186
95. Alkene Metathesis in total synthesis: Valienamine,
Agelastatin and Tonantzitlolone ............................ 188
96. Total Synthesis of the Tetracyclines ...................... 190
97. Enantioselective Construction of N-Heterocycles ........... 192
98. Stereocontrolled Construction of Cyclic Ethers ............ 194
99. Synthesis of the Proteosome Inhibitors Salinosporamide
A, Omuralide and Lactacystin .............................. 196
100.Synthesis of (-)-Sordaricin ............................... 198
101.Recent Advances in Carbocyclic Ketone Construction ........ 200
102.Stereoselective Construction of Carbocyclic Rings ......... 202
103.Asymmetric Transformation of Prochiral Carbocyclic
Rings ..................................................... 204
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