Organic Synthesis: State of the Art 2007 - 2009

253 Pages·2011·2.85 MB·English

by  Douglass F. Taber

Organic Synthesis
State of the Art 2007–2009
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Organic Synthesis
State of the Art 2007–2009
Douglass F. Taber
1
1

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Library of Congress Cataloging-in-Publication Data
Taber, D. F. (Douglass F.), 1948-
Organic synthesis : state of the art 2007–2009 / Douglass F. Taber.
p. cm.
ISBN 978-0-19-976454-9 (hardcover : alk. paper)
1. Organic compounds–Synthesis–Research. I. Title.
QD262.T284 2011
547'.2–dc22
2010020627

1 3 5 7 9 8 6 4 2

Printed in the United States of America
on acid-free paper
Contents
Preface xi
Organic Functional Group Interconversion and Protection
1. Best Synthetic Methods: Oxidation and Reduction 2
2. Functional Group Transformations 4
3. Best Synthetic Methods: Oxidation 6
4. Best Synthetic Methods: Reduction 8
5. Best Synthetic Methods: Functional Group Transformation 10
6. New Methods for Functional Group Conversion 12
7. Organic Functional Group Interconversion: (-)- β -Conhydrine (Barua)
and (+)-6'-Hydroxyarenarol (Anderson) 14
8. New Methods for Functional Group Conversion 16
9. Protection of Organic Functional Groups 18
10. Best Synthetic Methods: Functional Group Protection 20
11. Functional Group Protection 22
C-H Functionalization
12. Intermolecular and Intramolecular C-H Functionalization 24
13. C-H Functionalization to Form C-O, C-N, and C-C Bonds 26
14. Functionalization of C-H Bonds: The Baran Synthesis of
Dihydroxyeudesmane 28
Carbon-Carbon Bond Construction
15. New Methods for Carbon-Carbon Bond Construction 30
16. Best Synthetic Methods: Carbon-Carbon Bond Construction 32
17. C-C Single Bond Construction 34
18. Construction of Alkenes, Alkynes and Allenes 36
Reactions of Alkenes
19. Reduction, Oxidation and Homologation of Alkenes 38
20. Reactions of Alkenes 40
21. Selective Reactions of Alkenes 42
Alkene and Alkyne Metathesis
22. Developments in Alkene Metathesis 44
23. Developments in Alkene and Alkyne Metathesis 46
v
CONTENTS
24. Advances in Alkene and Alkyne Metathesis 48
25. Developments in Alkene Metathesis 50
26. Alkene Metathesis: Synthesis of Kainic Acid, Pladienolide B and
Amphidinolide Y 52
27. Alkene and Alkyne Metathesis: Phaseolinic Acid (Selvakumar),
Methyl 7-Dihydro-trioxacarcinoside B (Koert), Arglabin (Reiser)
and Amphidinolide V (Fürstner) 54
28. Alkene Metathesis: Synthesis of Panaxytriol (Lee), Isofagomine
(Imahori and Takahata), Elatol (Stoltz), 5-F -Isoprostane (Snapper),
2t
and Ottelione B (Clive) 56
29. Total Synthesis by Alkene Metathesis: Amphidinolide X
(Urpí/Vilarrasa), Dactylolide (Jennings), Cytotrienin A (Hayashi),
Lepadin B (Charette), Blumiolide C (Altmann) 58
Enantioselective Construction of Acyclic Stereogenic Centers
30. Enantioselective Assembly of Oxygenated Stereogenic Centers 60
31. Enantioselective Assembly of Aminated Stereogenic Centers 62
32. Enantioselective Preparation of Secondary Alcohols and Amines 64
33. Enantioselective Preparation of Alcohols and Amines 66
34. Enantioselective Synthesis of Alcohols and Amines 68
35. Enantioselective Assembly of Alkylated Stereogenic Centers 70
36. Enantioselective Construction of Alkylated Stereogenic Centers 72
37. Enantioselective Construction of Alkylated Centers 74
38. Enantioselective Construction of Alkylated Stereogenic Centers 76
39. Stereocontrolled Construction of Arrays of Stereogenic Centers 78
40. Enantioselective Construction of Arrays of Stereogenic Centers 80
41. Stereocontrolled Construction of Arrays of Stereogenic Centers 82
42. Practical Enantioselective Construction of Arrays of Stereogenic
Centers: The J ø rgensen Synthesis of the Autoregulator IM-2 84
Construction of C-O Rings
43. Enantioselective Synthesis of Lactones and Cyclic Ethers 86
44. Stereocontrolled C-O Ring Construction: The Fuwa/Sasaki
Synthesis of Attenol A 88
45. Stereoselective C-O Ring Construction: The Oguri-Oikawa
Synthesis of Lasalocid A 90
46. Stereocontrolled C-O Ring Construction: The Morimoto
Synthesis of (+)-Omaezakianol 92
47. Synthesis of Dysiherbaine (Hatakeyama), Jerangolid D (Markó)
and (+)-Spirolaxine Me Ether (Trost) 94
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) 96
vi
CONTENTS
49. C-O Ring Natural Products: (-)-Serotobenine (Fukuyama-Kan),
(-)-Aureonitol (Cox), Salmochelin SX (Gagné), Botcinin F (Shiina),
(-)-Saliniketal B (Paterson), Haterumalide NA (Borhan) 98
50. Complex Cyclic Ethers: (+)-Conocarpan (Hashimoto), (-)-Brevisamide
(Satake/Tachibana), (+)-Bruguierol A (Fañanás/Rodríguez),
(-)-Berkelic Acid (Snider), and (-)-Aigialomycin D (Harvey) 100
Construction of C-N Rings
51. New Methods for Stereoselective Construction of N-Containing Rings 102
52. Stereoselective C-N Ring Construction 104
53. New Methods for C-N Ring Construction 106
54. Stereocontrolled Construction of C-N Rings: The Vanderwal
Synthesis of Norfl uorocurarine 108
55. Alkaloid Synthesis: Paliurine F, Lepadiformine, and
7-Deoxypancratistatin 110
56. Adventures in Alkaloid Synthesis: (+)-α -Kainic Acid (Jung),
223AB (Ma), Pumiliotoxin 251F (Jamison),
Spirotryprostatin B (Trost), (-)-Drupacine (Stoltz) 112
57. Stereocontrolled Alkaloid Construction: Rhazinicine (Gaunt),
9- epi -Pentazocine (Zhai and Li), Fawcettidine (Dake),
Strychnine (Padwa), and Yohimbine (Jacobsen) 114
58. Alkaloid Synthesis: (-)-Aurantioclavine (Stoltz), (-)-Esermethole
(Nakao/Hiyama/Ogoshi), (-)-Kainic Acid (Tomooka),
Dasycarpidone (Bennasar), (-)-Cephalotaxine (Ishibashi) and
Lysergic Acid (Fujii/Ohno) 116
59. Alkaloid Synthesis: Crispine A (Zhou), Cermizine C (Zhang),
Tangutorine (Poupon), FR901483 (Kerr), Serratezomine A (Johnston) 118
Substituted Benzene Derivatives
60. Synthesis of Substituted Benzenes: The Carter Synthesis
of Siamenol 120
61. Preparation of Benzene Derivatives 122
62. Preparation of Benzene Derivatives: The Barrett Syntheses of
Dehydroaltenuene B and 15G256β 124
63. Substituted Benzenes: The Alvarez-Manzaneda Synthesis of
(-)-Taiwaniquinone G 126
Heteroaromatic Derivatives
64. Synthesis of Heteroaromatics 128
65. Preparation of Heteroaromatic Derivatives 130
66. Preparation of Heteroaromatics 132
67. Heterocycle Construction: The Chang Synthesis of
Louisianin C 134
vii
CONTENTS
Organocatalyzed C-C Ring Construction
68. Enantioselective Organocatalytic Construction of Carbocycles:
The Nicolaou Synthesis of Biyouyanagin A 136
69. Organocatalytic Ring Construction: The Corey
Synthesis of Coraxeniolide A 138
70. Enantioselective Organocatalyzed Construction of
Carbocyclic Rings 140
71. Organocatalytic C-C Ring Construction: (+)-Ricciocarpin A (List)
and (-)-Aromadendranediol (MacMillan) 142
Transition Metal Catalyzed C-C Ring Construction
72. Transition Metal-Mediated Construction of Carbocycles:
Dimethyl Gloiosiphone A (Takahashi), Pasteurestin A (Mulzer),
and Pentalenene (Fox) 144
73. Transition Metal-Mediated Ring Construction: The Yu Synthesis of
1-Desoxyhypnophilin 146
74. Transition Metal Catalyzed Construction of Carbocyclic Rings:
(-)-Hamigeran B 148
75. Transition Metal-Mediated C-C Ring Construction: The Stoltz
Synthesis of (-)-Cyanthiwigin F 150
Intermolecular and Intramolecular Diels-Alder Reactions
76. Intermolecular and Intramolecular Diels-Alder Reactions:
(-)-Oseltamivir (Fukuyama), Platensimycin (Yamamoto) and
11,12-Diacetoxydrimane (Jacobsen) 152
77. Intermolecular and Intramolecular Diels-Alder Reactions:
Platencin (Banwell), Platensimycin (Matsuo), (-)-Halenaquinone
(Trauner), (+)-Cassaine (Deslongchamps) 154
Stereocontrolled C-C Ring Construction
78. Stereocontrolled Carbocyclic Construction: The Trauner
Synthesis of the Shimalactones 156
79. Stereocontrolled Carbocyclic Construction: (-)-Mintlactone (Bates),
(-)-Gleenol (Kobayashi), (-)-Vibralactone C (Snider) 158
80. Stereocontrolled Carbocyclic Construction: The Mulzer
Synthesis of (-)-Penifulvin A 160
Classics in Total Synthesis
81. The Sammakia Synthesis of the Macrolide RK-397 162
82. The Maier Synthesis of Cruentaren A 164
83. The Betzer and Ardisson Synthesis of (+)-Discodermolide 166
84. The Smith Synthesis of (+)-Lyconadin A 168
85. The Rychnovsky Synthesis of Leucascandrolide A 170
86. The Burke Synthesis of (+)-Didemniserinolipid B 172
viii
CONTENTS
87. The Kozmin Synthesis of Spirofungin A 174
88. The Ley Synthesis of Rapamycin 176
89. The Toste Synthesis of (+)-Fawcettimine 178
90. The Bergman-Ellman Synthesis of (-)-Incarvillateine 180
91. The Roush Synthesis of (+)-Superstolide A 182
92. The Takayama Synthesis of (-)-Cernuine 184
93. The Wood Synthesis of Welwitindolinone A Isonitrile 186
94. The Paquette Synthesis of Fomannosin 188
95. The Zakarian Synthesis of (+)-Pinnatoxin A 190
96. The Hoveyda Synthesis of (-)-Clavirolide C 192
97. The Carter Synthesis of (-)-Lycopodine 194
98. The Johnson Synthesis of Zaragozic Acid C 196
99. The Keck Synthesis of Epothilone B 198
100. The Overman Syntheses of Nankakurines A and B 200
101. The Trost Synthesis of (-)-Ushikulide A 202
102. The Castle Synthesis of (-)-Acutumine 204
103. The Kobayashi Synthesis of (-)-Norzoanthamine 206
104. The Davies/Williams Synthesis of (-)-5-e pi -Vibansin E 208
Cumulative Author Index 211
Cumulative Reaction Index 225
ix