Organic Synthesis – State of the Art 2005–2007

DOUGLASS F. TABER, PhD, is Professor of Chemistry at the University of Delaware, Newark, Delaware. Professor Taber has published more than 170 articles in the organic chemistry field, and has authored eight chapters and several books. His research interests include the stereoselective synthesis of natural products, new methods in synthetic organic chemistry, and computational organometallic chemistry in organic synthesis.

Preface. 1. Synthesis of (-)- Littoralisone. 2. Enantiocontrolled Construction of Oxygenated and Animated Stereogenic Centers. 3. Catalytic Enantioselective Construction of Alkylated Stereogenic Centers. 4. Catalytic Enantioselective Aldol/Mannich Reactions Leading to Extended Arrays of Stereogenic Centers. 5. Alternative Strategies for the Construction of Extended Arrays of Stereogenic Centers. 6. Synthesis of(-)- Avrainvillamide and (+)- Stephacidin B. 7. Best Synthetic Methods: Oxidation. 8. Best Synthetic Methods: Reduction. 9. Selective Reactions of Alkenes. 10. Synthesis of the Potent FBBP12 Ligand Antascomicin B. 11. Best Synthetic Methods: Carbon-Carbon Bond Formation. 12. Enantioselective Construction of Quaternary Centers. 13. Pd-Mediated Arylation of Aromatic and Hetero Aromatic Rings. 14. The Overman Route to Gelsemine. 15. Stereoselective Construction of Oxygen Heterocycles. 16. Enantioselective Construction of Naturally-Occurring Cyclic Ethers. 17. Stereoselective Construction of Nitrogen Heterocycles. 19. The Stork Synthesis of (-)- Reserpine. 19. Stereocontrolled Construction of Azacyclic Natural Products. 20. Preparation of Benzene Derivatives. 21. Preparation of Heteroaromatics. 22. Preparation and Reactions of Carboxylic Acids, Esters and Amides. 23. The Boger Route to (-)- Vindoline. 24. Protection of C-O and C-N. 25. New Catalysts and Strategies for Alkene Metathesis. 26. Creative Applications of Alkene and Alkyne Metathesis in Total Synthesis: (+)-8epi-Xanthatin, (+)-Longicin, Latrunculin A, and Garsubellin A. 27. Synthesis of Erythronolide A. 28. Best Synthetic Methods: C-C Bond Formation. 29. Catalytic Enantioselective Homologation of Aldehydes to Alcohols and Amines. 30. Catalytic Enantioselective Construction of Alkylated Stereogenic Centers. 31. Enantioselective Construction of Arrays of Stereogenic Centers. 32. Adventures in Complex Indole Synthesis: (-)-Fixherindole I, (+)-Fischerindole G and (+)-Weltwitindolinone A. 33. New Dienes and Dienophiles for Intermolecular and Intramolecular Diels-Alder Cycloaddtions. 34. Organocatalytic Preparation of Enantiomerically-Pure Carbocycles. 35. Carbocycle Construction by the Opening of Strained Rings: Synthesis of Tremulenolide A. 36. The Corey Route to the Dolabellanes: Isoedunol and P-Araneosene. 37. Transition-Metal Catalyzed Enantioselective Ring Construction. 38. Best Synthetic Methods: Functional Group Transformation. 39. Selective Reactions of Alkenes. 40. Synthesis and Absolute Stereochemical Assignment of (-)-Galbulimima Alkaloid 13. 41. Preparation of Benzene Derivatives. 42. Preparation of Heteroaromatic Derivatives. 43. Functional Group Transformation. 44. Functional Group Protection. 45. The Leighton Synthesis of Dolabelide D. 46. Stereocontrolled Construction of N-Heterocycles. 47. Stereocontrolled Construction of O-Heterocycles. 48. Stereocontrolled Synthesis of O-Heterocyclic Natural Products. 49. The Ready Synthesis of (-)-Nigellamine A2. 50. Advances in the Diels-Alder Reaction: Synthesis of (+)-Lycoridine and of Dolabellatrienone. 51. Enantioselective Carbocyclic Construction. 52. Transition Metal Mediated Carbocyclic Construction. 53. Synthesis of (-)-Colombiasin A and (-)-Elisapterosin B. 54. Enantioselective Synthesis of C-N Ring Containing Natural Products. 55. New Catalysts and Strategies for Alkene and Alkyne Metathesis. 56. Heterocyclic Natural Products by Alkene Metathesis. 57. Carbobyclic Natural Products by Alkene Metathesis. 58. The Crimmins Synthesis of (+)-SCH 351448. 59. Enantioselective Construction of Alcohols and Amines. 60. Enantioselective Construction of Alkylated Stereogenic Centers. 61. Enantioselective Construction of Arrays of Stereogenic Centers. 62. The Sorensen Synthesis of (-)-Guanacastepene E. 63. Selective Reactions of Alkenes. 64. Best Synthetic Methods: C-C Bond Formation. 65. Functional Group Protection and Deprotection. 66. The Nicolaou Synthesis of Platensimycin. 67. Stereocontrolled C-O Ring Construction. 68. Stereocontrolled Natural Product Synthesis: Cyclic Ethers and Macrolides. 69. Stereocontrolled C-N Ring Construction. 70. Stereocontrolled Alkaloid Total Synthesis. 71. The Fukuyama Synthesis of Morphine. 73. Oxidation and Reduction in Organic Synthesis. 73. Interconversion of Organic Functional Groups. 74. Best Synthetic Methods: Carbon-Carbon Bond Formation. 75. The Overman Synthesis of (-)-Sarah A. 76. Recent Developments in Alkene Metathesis. 77. Pushing the Limits of Alkene Metathesis in Natural Product Synthesis. 78. Preparation of Benzene Derivatives. 79. The Padwa Synthesis of Aspidophytidine. 80. Synthesis of Heteroaromatics. 8 1. Enantioselective Construction of Alcohols and Amines. 82. Enantioselective Construction of Alkylated Stereogenic Centers. 83. Enantioselective Construction of Arrays of Stereogenic Centers. 84. The Gin Synthesis of Nominine. 85. The Intramolecular Diels-Alder Reaction in Natural Product Synthesis. 86. Catalytic Enantioselective Carbon-Carbon Ring Construction. 87. New Directions in C-C Ring Construction: The Overman Synthesis of Guanacastepene N. 88. The Pettus Synthesis of (+)-Rishirilide B. 89. Selective Reactions of Alkenes. 90. Selective C-H Functionalization. 91. New Methods for Carbon-Carbon Bond Formation. 92. The Nakada Synthesis of (+)-Digitoxigenin. 93. Preparation of Benzene Derivatives. 94. Preparation of Heteroaromatics: The Movassaghi Synthesis of (+)-Chimonanthine. 95. Organic Functional Group Transformation. 96. Organic Functional Group Protection. 97. The Trost Synthesis of (-)-Terpestacin. 98. Stereoselective C-N Ring Construction. 99. Stereoselective C-0 Ring Construction. 100. Synthesis of (-)-Blepharocalyxin D, (-)-Lasonolide A, and Attenol A. 101. The Dark Synthesis of Vigulariol. 102. Enantioselective Organocatalytic Synthesis of Carbocycles: The Iwabuchi Synthesis of (+)-Juvabione. 103. Transition-metal Mediated Synthesis of Carbocycles: The Snapper Synthesis of Pleocarpenone. 104. Enantioselective Construction of Carbocycles: The Williams Synthesis of (+)-Fusicoauritone. 105. C-H Functionalization: The White Reagent. Author Index. Reaction Index.