Organic Synthesis : State of the Art 2007 - 2009

Organic synthesis is a vibrant and rapidly evolving field; we can now cyclize amines directly onto alkenes. Like the first two books in this series, Organic Synthesis: State of the Art 2003-2005 and Organic Synthesis: State of the Art 2005-2007, this reference leads readers quickly to the most important recent developments. Two years of Taber's popular weekly online column, "Organic Chemistry Highlights", as featured on the organic-chemistry.org website, are consolidated here, with cumulative indices of all three volumes in this series. Important topics that are covered range from powerful new methods for C-C bond construction to asymmetric organocatalysis and direct C-H functionalization. This go-to reference focuses on the most important recent developments in organic synthesis, and includes a succinct analysis of the significance and applicability of each new synthetic method. It details and analyzes more than twenty complex total syntheses, including the Sammakia synthesis of the Macrolide RK-397, the Ley synthesis of Rapamycin, and the Kobayashi synthesis of (-)-Norzoanthamine. Cover......Page 1 Contents......Page 6 Preface......Page 12 Organic Functional Group Interconversion and Protection......Page 14 1. Best Synthetic Methods: Oxidation and Reduction......Page 15 2. Functional Group Transformations......Page 17 3. Best Synthetic Methods: Oxidation......Page 19 4. Best Synthetic Methods: Reduction......Page 21 5. Best Synthetic Methods: Functional Group Transformation......Page 23 6. New Methods for Functional Group Conversion......Page 25 7. Organic Functional Group Interconversion: (-)-β-Conhydrine (Barua) and (+)-6'-Hydroxyarenarol (Anderson)......Page 27 8. New Methods for Functional Group Conversion......Page 29 9. Protection of Organic Functional Groups......Page 31 10. Best Synthetic Methods: Functional Group Protection......Page 33 11. Functional Group Protection......Page 35 12. Intermolecular and Intramolecular C-H Functionalization......Page 37 13. C-H Functionalization to Form C-O, C-N, and C-C Bonds......Page 39 14. Functionalization of C-H Bonds: The Baran Synthesis of Dihydroxyeudesmane......Page 41 15. New Methods for Carbon-Carbon Bond Construction......Page 43 16. Best Synthetic Methods: Carbon-Carbon Bond Construction......Page 45 17. C-C Single Bond Construction......Page 47 18. Construction of Alkenes, Alkynes and Allenes......Page 49 19. Reduction, Oxidation and Homologation of Alkenes......Page 51 20. Reactions of Alkenes......Page 53 21. Selective Reactions of Alkenes......Page 55 22. Developments in Alkene Metathesis......Page 57 23. Developments in Alkene and Alkyne Metathesis......Page 59 24. Advances in Alkene and Alkyne Metathesis......Page 61 25. Developments in Alkene Metathesis......Page 63 26. Alkene Metathesis: Synthesis of Kainic Acid, Pladienolide B and Amphidinolide Y......Page 65 27. Alkene and Alkyne Metathesis: Phaseolinic Acid (Selvakumar), Methyl 7-Dihydro-trioxacarcinoside B (Koert), Arglabin (Reiser) and Amphidinolide V (Fürstner)......Page 67 28. Alkene Metathesis: Synthesis of Panaxytriol (Lee), Isofagomine (Imahori and Takahata), Elatol (Stoltz), 5-F[Sub(2t)]-Isoprostane (Snapper), and Ottelione B (Clive)......Page 69 29. Total Synthesis by Alkene Metathesis: Amphidinolide X (Urpí/Vilarrasa), Dactylolide (Jennings), Cytotrienin A (Hayashi), Lepadin B (Charette), Blumiolide C (Altmann)......Page 71 30. Enantioselective Assembly of Oxygenated Stereogenic Centers......Page 73 31. Enantioselective Assembly of Aminated Stereogenic Centers......Page 75 32. Enantioselective Preparation of Secondary Alcohols and Amines......Page 77 33. Enantioselective Preparation of Alcohols and Amines......Page 79 34. Enantioselective Synthesis of Alcohols and Amines......Page 81 35. Enantioselective Assembly of Alkylated Stereogenic Centers......Page 83 36. Enantioselective Construction of Alkylated Stereogenic Centers......Page 85 37. Enantioselective Construction of Alkylated Centers......Page 87 38. Enantioselective Construction of Alkylated Stereogenic Centers......Page 89 39. Stereocontrolled Construction of Arrays of Stereogenic Centers......Page 91 40. Enantioselective Construction of Arrays of Stereogenic Centers......Page 93 41. Stereocontrolled Construction of Arrays of Stereogenic Centers......Page 95 42. Practical Enantioselective Construction of Arrays of Stereogenic Centers: The Jørgensen Synthesis of the Autoregulator IM-2......Page 97 43. Enantioselective Synthesis of Lactones and Cyclic Ethers......Page 99 44. Stereocontrolled C-O Ring Construction: The Fuwa/Sasaki Synthesis of Attenol A......Page 101 45. Stereoselective C-O Ring Construction: The Oguri-Oikawa Synthesis of Lasalocid A......Page 103 46. Stereocontrolled C-O Ring Construction: The Morimoto Synthesis of (+)-Omaezakianol......Page 105 47. Synthesis of Dysiherbaine (Hatakeyama), Jerangolid D (Markó) and (+)-Spirolaxine Me Ether (Trost)......Page 107 48. C-O Ring Containing Natural Products: Paeonilactone B (Taylor), Deoxymonate B (de la Pradilla), Sanguiin H-5 (Spring), Solandelactone A (White), Spirastrellolide A (Paterson)......Page 109 49. C-O Ring Natural Products: (-)-Serotobenine (Fukuyama-Kan), (-)-Aureonitol (Cox), Salmochelin SX (Gagné), Botcinin F (Shiina), (-)-Saliniketal B (Paterson), Haterumalide NA (Borhan)......Page 111 50. Complex Cyclic Ethers: (+)-Conocarpan (Hashimoto), (-)-Brevisamide (Satake/Tachibana), (+)-Bruguierol A (Fañanás/Rodríguez), (-)-Berkelic Acid (Snider), and (-)-Aigialomycin D (Harvey)......Page 113 51. New Methods for Stereoselective Construction of N-Containing Rings......Page 115 52. Stereoselective C-N Ring Construction......Page 117 53. New Methods for C-N Ring Construction......Page 119 54. Stereocontrolled Construction of C-N Rings: The Vanderwal Synthesis of Norfluorocurarine......Page 121 55. Alkaloid Synthesis: Paliurine F, Lepadiformine, and 7-Deoxypancratistatin......Page 123 56. Adventures in Alkaloid Synthesis: (+)-α-Kainic Acid (Jung), 223AB (Ma), Pumiliotoxin 251F (Jamison), Spirotryprostatin B (Trost), (-)-Drupacine (Stoltz)......Page 125 57. Stereocontrolled Alkaloid Construction: Rhazinicine (Gaunt), 9-epi-Pentazocine (Zhai and Li), Fawcettidine (Dake), Strychnine (Padwa), and Yohimbine (Jacobsen)......Page 127 58. Alkaloid Synthesis: (-)-Aurantioclavine (Stoltz), (-)-Esermethole (Nakao/Hiyama/Ogoshi), (-)-Kainic Acid (Tomooka), Dasycarpidone (Bennasar), (-)-Cephalotaxine (Ishibashi) and Lysergic Acid (Fujii/Ohno)......Page 129 59. Alkaloid Synthesis: Crispine A (Zhou), Cermizine C (Zhang), Tangutorine (Poupon), FR901483 (Kerr), Serratezomine A (Johnston)......Page 131 60. Synthesis of Substituted Benzenes: The Carter Synthesis of Siamenol......Page 133 61. Preparation of Benzene Derivatives......Page 135 62. Preparation of Benzene Derivatives: The Barrett Syntheses of Dehydroaltenuene B and 15G256 β......Page 137 63. Substituted Benzenes: The Alvarez-Manzaneda Synthesis of (-)-Taiwaniquinone G......Page 139 64. Synthesis of Heteroaromatics......Page 141 65. Preparation of Heteroaromatic Derivatives......Page 143 66. Preparation of Heteroaromatics......Page 145 67. Heterocycle Construction: The Chang Synthesis of Louisianin C......Page 147 68. Enantioselective Organocatalytic Construction of Carbocycles: The Nicolaou Synthesis of Biyouyanagin A......Page 149 69. Organocatalytic Ring Construction: The Corey Synthesis of Coraxeniolide A......Page 151 70. Enantioselective Organocatalyzed Construction of Carbocyclic Rings......Page 153 71. Organocatalytic C-C Ring Construction: (+)-Ricciocarpin A (List) and (-)-Aromadendranediol (MacMillan)......Page 155 72. Transition Metal-Mediated Construction of Carbocycles: Dimethyl Gloiosiphone A (Takahashi), Pasteurestin A (Mulzer), and Pentalenene (Fox)......Page 157 73. Transition Metal-Mediated Ring Construction: The Yu Synthesis of 1-Desoxyhypnophilin......Page 159 74. Transition Metal Catalyzed Construction of Carbocyclic Rings: (-)-Hamigeran B......Page 161 75. Transition Metal-Mediated C-C Ring Construction: The Stoltz Synthesis of (-)-Cyanthiwigin F......Page 163 76. Intermolecular and Intramolecular Diels-Alder Reactions: (-)-Oseltamivir (Fukuyama), Platensimycin (Yamamoto) and 11,12-Diacetoxydrimane (Jacobsen)......Page 165 77. Intermolecular and Intramolecular Diels-Alder Reactions: Platencin (Banwell), Platensimycin (Matsuo), (-)-Halenaquinone (Trauner), (+)-Cassaine (Deslongchamps)......Page 167 78. Stereocontrolled Carbocyclic Construction: The Trauner Synthesis of the Shimalactones......Page 169 79. Stereocontrolled Carbocyclic Construction: (-)-Mintlactone (Bates), (-)-Gleenol (Kobayashi), (-)-Vibralactone C (Snider)......Page 171 80. Stereocontrolled Carbocyclic Construction: The Mulzer Synthesis of (-)-Penifulvin A......Page 173 81. The Sammakia Synthesis of the Macrolide RK-397......Page 175 82. The Maier Synthesis of Cruentaren A......Page 177 83. The Betzer and Ardisson Synthesis of (+)-Discodermolide......Page 179 84. The Smith Synthesis of (+)-Lyconadin A......Page 181 85. The Rychnovsky Synthesis of Leucascandrolide A......Page 183 86. The Burke Synthesis of (+)-Didemniserinolipid B......Page 185 87. The Kozmin Synthesis of Spirofungin A......Page 187 88. The Ley Synthesis of Rapamycin......Page 189 89. The Toste Synthesis of (+)-Fawcettimine......Page 191 90. The Bergman-Ellman Synthesis of (-)-Incarvillateine......Page 193 91. The Roush Synthesis of (+)-Superstolide A......Page 195 92. The Takayama Synthesis of (-)-Cernuine......Page 197 93. The Wood Synthesis of Welwitindolinone A Isonitrile......Page 199 94. The Paquette Synthesis of Fomannosin......Page 201 95. The Zakarian Synthesis of (+)-Pinnatoxin A......Page 203 96. The Hoveyda Synthesis of (-)-Clavirolide C......Page 205 97. The Carter Synthesis of (-)-Lycopodine......Page 207 98. The Johnson Synthesis of Zaragozic Acid C......Page 209 99. The Keck Synthesis of Epothilone B......Page 211 100. The Overman Syntheses of Nankakurines A and B......Page 213 101. The Trost Synthesis of (-)-Ushikulide A......Page 215 102. The Castle Synthesis of (-)-Acutumine......Page 217 103. The Kobayashi Synthesis of (-)-Norzoanthamine......Page 219 104. The Davies/Williams Synthesis of (-)-5-epi-Vibansin E......Page 221 B......Page 224 C......Page 225 F......Page 226 H......Page 227 J......Page 228 L......Page 229 M......Page 230 O......Page 231 R......Page 232 S......Page 233 V......Page 234 Y......Page 235 Z......Page 236 A......Page 238 C......Page 242 E......Page 243 G......Page 244 I......Page 245 M......Page 246 N......Page 247 P......Page 249 R......Page 251 S......Page 252 W......Page 253 This book is a useful field guide for the practicing organic chemist and a rich introduction for the student. Functional group transformations, new catalysts, and improved enantioselective methods are included. Many current total syntheses are also discussed in detail.