Printed in the United States of America on acid-free
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
(Ваruа) 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
24 Advances in Alkene and Alkyne Metathesis .................... 48
25 Developments in Alkene Metathesis ........................... 50
26 Alkene Metathesis: Synthesis of Kainic Acid, Pladienolide
В and Amphidinolide Y ....................................... 52
27 Alkene and Alkyne Metathesis: Phaseolinic Acid
(Selvakumar), Methyl 7-Dihydro-trioxacarcinoside В
(Koert), Arglabin (Reiser) and Amphidinolide V (Fürstner) ... 54
28 Alkene Metathesis: Synthesis of Panaxytriol (Lee),
Isofagomine (Imahori and Takahata), Elatol (Stoltz),
5-F2t-Isoprostane (Snapper), and Ottelione В (Clive) ........ 56
29 Total Synthesis by Alkene Metathesis: Amphidinolide X
(Urpi/Vilarrasa), Dactylolide (Jennings), Cytotrienin A
(Hayashi), Lepadin В (Charette), Blumiolide С (Altmann) ..... 58
Enantioselective Construction of Acyclic Stereogenic Centers
30 Enantioselective Assembly of Oxygenated Stereogenic
Centers ..................................................... 60
31 Enantioselective Assembly of Animated 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 Jorgensen Synthesis of the
Autoregulator IM-2 .......................................... 84
Construction of C-O Rings
43 Enantioselective Synthesis of Lactones and Cyclic Ethers .... 86
44 Stereocontrolled C-0 Ring Construction: The Fuwa/Sasaki
Synthesis of Attenol A ...................................... 88
45 Stereoselective C-0 Ring Construction: The Oguri-Oikawa
Synthesis of Lasalocid A .................................... 90
46 Stereocontrolled C-0 Ring Construction: The Morimoto
Synthesis of (+)-Omaezakianol ............................... 92
47 Synthesis of Dysiherbaine (Hatakeyama), Jerangolid D
(Marko) and (+)-Sp%olaxine Me Ether (Trost) ................. 94
48 C-O Ring Containing Natural Products: Paeonilactone В
(Taylor), Deoxymonate В (de la Pradilla), Sanguiin H-5
(Spring), Solandelactone A (White), Spirastrellolide A
(Paterson) .................................................. 96
49 C-0 Ring Natural Products: (-)-Serotobenine
(Fukuyama-Kan), (-)-Aureonitol(Cox), Salmochelin SX
(Gagné), Botcinin F (Shiina), (-)-Saliniketal В
(Paterson), Haterumalide NA (Borhan) ........................ 98
50 Complex Cyclic Ethers: (+)-Conocarpan (Hashimoto),
(-)-Brevisamide (Satake/Tachibana), (+)-Bruguierol A
(Fañanás/Rodriguez), (-)-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 Norfluorocurarine
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 В (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 С
(Zhang), Tangutorine (Poupon), FR901483 (Kerr),
Serratezomine A (Johnston) ................................. 118
Substituted Benzene Derivatives
60 Synthesis of Substituted Benzenes: The Carter Synthesis
ofSiamenol .................................................
61 Preparation of Benzene Derivatives ......................... 122
62 Preparation of Benzene Derivatives: The Barrett Syntheses
of Dehydroaltenuene В 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 С ............................................... 134
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 В ..................................... 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 С (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 BetzU»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 В ............ 172
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 С ................. 192
97 The Carter Synthesis of (-)-Lycopodine ..................... 194
98 The Johnson Synthesis of Zaragozic Acid С .................. 196
99 The Keck Synthesis of Epothilone В ......................... 198
100 The Overman Syntheses of Nankakurines A and В ............. 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-epi-Vibansin E ..... 208
Cumulative Author Index ....................................... 211
Cumulative Reaction Index ..................................... 225
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