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Organic Synthesis - State of the Art 2003
2005

Douglass F. Taber

Hardcover, 216 Pages
First Edition, 2006
ISBN: 0-470-05331-3
Wiley-Interscience

Description

The first in a new series, Organic Synthesis: State of the Art 2003–2005 pulls together two years' worth of Taber's popular and highly-regarded column, and comprises a concise, extremely useful overview of current accomplishments in the field of organic synthesis. The 103 articles in this volume review the leading synthetic procedures developed over the last two years, discussing their significance and their applications. The more than 100 reactions covered in this First Volume of the series include:

Enhanced by author and subject-transformation indices, Organic Synthesis: State of the Art 2003–2005 offers chemists an effective, much-needed way to stay abreast of what's new and exciting in their field.

Editorial Review

Four years ago, Professor Taber contacted me to see whether I had any interest in publishing a weekly column he would write. At the time, the inquiry caught me by surprise, since the web project was nowhere near as elaborate as it is today. I believe that it was the publication of Douglass F. Taber’s "Highlights" that provided the initial impetus to invest further in original content. In this way, the contributions from Douglass played an essential catalytic role in accelerating the development of this project.

From my perspective, the “Highlights” are a good opportunity to glean information on really interesting reactions each week, and once the curiosity has been piqued one can investigate further by consulting the cited literature. The number of page views for these Highlights continues to increase, which is another indication of high interest by visitors to the site in having such short reviews published here. The numerous responses by readers have inspired us to continue producing this column, as have reviews such as that by Kilian Muniz, who wrote, “These days, when such an overwhelming amount of material is published, it is convenient to be able to access summarized information and gain a quick overview of a current topic.” (Angew. Chem. Int. Ed. 2004, 43, 2468. DOI).

Recently, Douglass decided to publish a first collection of these Highlights in book form, and found in Wiley a publisher who was enthusiastic about the idea. The book "Organic Synthesis - State of the Art 2003
2005" is the end result. Now it comes down to penning an unbiased review of this work, which is a bit of a challenge considering that all of the content has been published in this same site over the past four years. However, readers can now simply check for themselves whether or not to purchase "Organic Synthesis - State of the Art" by referring to Douglass F. Taber’s previous publications in our "Highlights".

To the price-conscious reader, the question of why to acquire the book naturally arises. The author provides the following answer to this question: "So, why this book, if the columns are already available free on the Web? First, there are a lot of them, 103 in this book. It is convenient having them all in one place. Too, there is an index of senior authors, and a subject/transformation index. Most important, this collection of columns, taken together, is an effective overview of the most important developments in organic synthesis over the two-year period."

I believe that anyone who reads the web edition on a weekly basis, and enjoys the topical exposure to the interesting reactions published there, should seriously consider purchasing the book. My hope for the author is that sales of this work will be brisk. For one thing, it will confirm the high level of interest in Douglass's work and in these Highlights; at the same time, it will also compensate the effort made each week to produce these columns, the free availability of which has already benefited many. I will be very pleased if we can successfully produce such chemistry content not only when it is freely accessible on the web, but also when available in book form, and I hope that we are able to carry along the content in both media as long as possible. You the readers can do your part!

Contents

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