Organic Synthesis: State of the Art 2005-2007 (Organic Synthesis: State of the Art)

243 Pages·2008·8.03 MB·English

by  Douglass F. Taber

Organic Synthesis
State of the Art 2005-2007
Douglass F. Taber
University of Delaware
Newark, DE
WILEY
A JOHN WILEY & SONS, INC., PUBLICATION
This Page Intentionally Left Blank
Organic Synthesis
State of the Art 2005-2007
This Page Intentionally Left Blank
Organic Synthesis
State of the Art 2005-2007
Douglass F. Taber
University of Delaware
Newark, DE
WILEY
A JOHN WILEY & SONS, INC., PUBLICATION
Copyright I2 008 by John Wiley & Sons, Inc All rights reserved
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Library of Congress Cataloging-in-Publication Data is available.
ISBN-978-0-470-28849-8
Printed in the United States of America.
1 0 9 8 7 6 5 4 3 2 1
Contents
Preface xi
1. Synthesis of (-)- Littoralisone 1
2. Enantiocontrolled Construction of Oxygenated and Animated 3
Stereogenic Centers
3. Catalytic Enantioselective Construction of Alkylated 5
Stereogenic Centers
4. Catalytic Enantioselective Aldol/Mannich Reactions Leading to 7
Extended Arrays of Stereogenic Centers
5. Alternative Strategies for the Construction of Extended Arrays of 9
Stereogenic Centers
6. Synthesis of(-)- Avrainvillamide and (+)- Stephacidin B 11
7. Best Synthetic Methods: Oxidation 13
8. Best Synthetic Methods: Reduction 15
9. Selective Reactions of Alkenes 17
10. Synthesis of the Potent FBBP12 Ligand Antascomicin B 19
11. Best Synthetic Methods: Carbon-Carbon Bond Formation 21
12. Enantioselective Construction of Quaternary Centers 23
13. Pd-Mediated Arylation of Aromatic and Hetero Aromatic Rings 25
14. The Overman Route to Gelsemine 27
15. Stereoselective Construction of Oxygen Heterocycles 29
16. Enantioselective Construction of Naturally-Occurring 31
Cyclic Ethers
17. Stereoselective Construction of Nitrogen Heterocycles 33
18. The Stork Synthesis of (-)- Reserpine 35
19. Stereocontrolled Construction of Azacyclic Natural Products 37
20. Preparation of Benzene Derivatives 39
21. Preparation of Heteroaromatics 41
V
CONTENTS
22. Preparation and Reactions of Carboxylic Acids, Esters and Amides 43
23. The Boger Route to (-)- Vindoline 45
24. Protection of C-0 and C-N 47
25. New Catalysts and Strategies for Alkene Metathesis 49
26. Creative Applications of Alkene and Alkyne Metathesis in Total 51
Synthesis: (+)-%epi-Xanthatin, (+)-Longicin, Latrunculin A, and
Garsubellin A
27. Synthesis of Erythronolide A 53
28. Best Synthetic Methods: C-C Bond Formation 55
29. Catalytic Enantioselective Homologation of Aldehydes to Alcohols 57
and Amines
30. Catalytic Enantioselective Construction of Alkylated Stereogenic 59
Centers
31. Enantioselective Construction of Arrays of Stereogenic Centers 61
32. Adventures in Complex Indole Synthesis: (-)-Fixherindole I, 63
(+)-Fischerindole G and (+)-Weltwitindolinone A
33. New Dienes and Dienophiles for Intermolecular and Intramolecular 65
Diels-Alder Cycloaddtions
34. Organocatalytic Preparation of Enantiomerically-Pure Carbocycles 67
35. Carbocycle Construction by the Opening of Strained Rings: Synthesis 69
of Tremulenolide A
36. The Corey Route to the Dolabellanes: Isoedunol and P-Araneosene 71
37. Transition-Metal Catalyzed Enantioselective Ring Construction 73
38. Best Synthetic Methods: Functional Group Transformation 75
39. Selective Reactions of Alkenes 77
40. Synthesis and Absolute Stereochemical Assignment of 79
(-)-Galbulimima Alkaloid 13
41. Preparation of Benzene Derivatives 81
42. Preparation of Heteroaromatic Derivatives 83
43. Functional Group Transformation 85
44. Functional Group Protection 87
45. The Leighton Synthesis of Dolabelide D 89
vi
CONTENTS
46. Stereocontrolled Construction of N-Heterocycles 91
47. Stereocontrolled Construction of 0-Heterocycles 93
48. Stereocontrolled Synthesis of 0-Heterocyclic Natural Products 95
49. The Ready Synthesis of (-)-Nigellamine A, 97
50. Advances in the Diels-Alder Reaction: Synthesis of (+)-Lycoridine 99
and of Dolabellatrienone
5 1. Enantioselective Carbocyclic Construction 101
52. Transition Metal Mediated Carbocyclic Construction 103
53. Synthesis of (-)-Colombiasin A and (-)-Elisapterosin B 105
54. Enantioselective Synthesis of C-N Ring Containing Natural Products 107
55. New Catalysts and Strategies for Alkene and Alkyne Metathesis 109
56. Heterocyclic Natural Products by Alkene Metathesis 111
57. Carbobyclic Natural Products by Alkene Metathesis 113
58. The Crimmins Synthesis of (+)-SCH 351448 115
59. Enantioselective Construction of Alcohols and Amines 117
6 1. Enantioselective Construction of Alkylated Stereogenic Centers 119
6 1. Enantioselective Construction of Arrays of Stereogenic Centers 121
62. The Sorensen Synthesis of (-)-Guanacastepene E 123
63. Selective Reactions of Alkenes 125
64. Best Synthetic Methods: C-C Bond Formation 127
65. Functional Group Protection and Deprotection 129
66. The Nicolaou Synthesis of Platensimycin 131
67. Stereocontrolled C-0 Ring Construction 133
68. Stereocontrolled Natural Product Synthesis: Cyclic Ethers and 135
Macrolides
69. Stereocontrolled C-N Ring Construction 137
70. Stereocontrolled Alkaloid Total Synthesis 139
71. The Fukuyama Synthesis of Morphine 141
73. Oxidation and Reduction in Organic Synthesis 143
73. Interconversion of Organic Functional Groups 145
vii