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Review
. 2013 Aug 14;113(8):5701-65.
doi: 10.1021/cr4000144. Epub 2013 Jun 17.

Chemistry of bridged lactams and related heterocycles

Michal Szostak  1 , Jeffrey Aubé
Affiliations
Review

Chemistry of bridged lactams and related heterocycles

Michal Szostak et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Resonance descriptions of the amide bond.
Figure 2
Figure 2
Types of distorted amide bonds: a) steric repulsion; b) conformational effects; c) anomeric amides; d) steric restriction.
Figure 3
Figure 3
Scope of the review: a) types of bridged lactams; b) heterocycles with 1-aza-bridged scaffold.
Figure 4
Figure 4
Winkler-Dunitz distortion parameters of amide bonds.
Figure 5
Figure 5
Comparison of anti-Bredt olefins and lactams: a) calculated olefin strain energy of bridged olefins by Schleyer; b) year of synthesis of the corresponding bridged lactam. (please use double-column format for Figure 5)
Figure 6
Figure 6
Role of methyl substituents in synthesisof 1-aza-2-adamantanones from the corresponding amino acids.
Figure 7
Figure 7
Atropoisomers formed in Witkop photocyclization of (N-chloroacetylpiperidyl)indole 150.
Figure 8
Figure 8
Benzofused bridged lactams: a) Benzo-1-azabicyclo[4.3.1]decan-9-one by Qiu; b) Bridged lactams derived from Tröger’s base by Wärnmark.
Figure 9
Figure 9
Design of 1-azabicyclo[4.1.1]octan-7-ones with increased stability: a) nucleophilic attack on lactam carbonyl group; b) deprotonation of bridgehead methine proton.
Figure 10
Figure 10
a) Heteroatom-containing derivatives of bridged lactams; b) Stabilizing resonance interaction in bridged ureas and urethanes.
Figure 11
Figure 11
Design of conformationally-constrained analogues by Smissman: a) anticonvulsant and anti-steroid drugs containing planar amide bonds; b) potential analogues containing bridged amide bonds (“smissmanones”).
Figure 12
Figure 12
Determination of pKa of 2-quinuclidones by Pracejus (44, 46a–b) and Yakhontov (46c)
Figure 13
Figure 13
Hydrolysis of Bridged Homologues of1-Azabicyclo[3.3.1]nonan-2-oneby Judd
Figure 14
Figure 14
Hydrolysis of bridged urethanes by Hall.
Figure 15
Figure 15
a) Bridged Lactam Bearing Epoxide by Paquette; b) Tricyclic Bridged Lactam by Aubé
Scheme 1
Scheme 1
Early Attempts of Synthesis of Bridged Lactams
Scheme 2
Scheme 2
Synthesis of 2-Quinuclidone during Autoxidation of Quininone by Doering and Chanley
Scheme 3
Scheme 3
Synthesis of Unsubstituted 2-Quinuclidone by Yakhontov
Scheme 4
Scheme 4
Synthesis of 6,6-Dimethyl-2-Quinuclidone by Pracejus (please use double-column format for Scheme 4)
Scheme 5
Scheme 5
Synthesis of Substituted 2-Quinuclidones by Pracejus and Yakhontov
Scheme 6
Scheme 6
Improved Synthesis of 6,6,7,7-Tetramethyl-2-Quinuclidone by Greenberg
Scheme 7
Scheme 7
Synthesis of 2-Quinuclidonium Tetrafluoroborate by Tani and Stoltz
Scheme 8
Scheme 8
Proposed Mechanism for Schmidt Reaction of 3-Azidoalkyl Ketone 51
Scheme 9
Scheme 9
Synthesis of Unsubstituted 2-Quinuclidone in a Gas Phase by Stoltz
Scheme 10
Scheme 10
Synthesis of Benzo-2-Quinuclidone by Blackburn
Scheme 11
Scheme 11
Synthesis of Benzo-2-Quinuclidones by Brown
Scheme 12
Scheme 12
Synthesis of Expanded Ring Systems of Benzo-2-Quinuclidones by Brown
Scheme 13
Scheme 13
Synthesis of 2-Quinuclidones under Gif Conditions by Jankowski
Scheme 14
Scheme 14
Synthesis of 2-Quinuclidones from Modified Cinchona Alkaloids by Hoffmann
Scheme 15
Scheme 15
Synthesis of Bridged Imides from Kemp Triacid by Rebek
Scheme 16
Scheme 16
Synthesis of 1-Aza-2-adamantanone (“the Most Twisted Amide”) by Kirby
Scheme 17
Scheme 17
Synthesis of Benzo-1-aza-2-adamantanone by Coe
Scheme 18
Scheme 18
Synthesis of 1-Azabicyclo[3.3.1]nonan-2-one 87 by Walker
Scheme 19
Scheme 19
a) Condensation to 1-Azabicyclo[3.3.1]nonan-2-one by Albertson; b) Revision of Proposed Structure of 90
Scheme 20
Scheme 20
Synthesis of 1-Azabicyclo[3.3.1]nonan-2-one by Hall
Scheme 21
Scheme 21
Synthesis of 5-Phenyl-1-Azabicyclo[3.3.1]nonan-2-one by Buchanan
Scheme 22
Scheme 22
Improved Synthesis of 1-Azabicyclo[3.3.1]nonan-2-one by Steliou
Scheme 23
Scheme 23
Application of Bu2SnO in Synthesis of 1-Azabicyclo[3.3.1]nonane-2,6-dione by Sim
Scheme 24
Scheme 24
Application of Bu2SnO in Synthesis of (+)-(R)-1-Azabicyclo[3.3.1]nonan-2-oneby Gerlach
Scheme 25
Scheme 25
Synthesis of 4-Methyl-5-tosyl-1-azabicyclo[3.3.1]nonan-2-ones by Najera
Scheme 26
Scheme 26
Synthesis of Quinolino-1-Azabicyclo[3.3.1]nonan-2-ones by Cuny
Scheme 27
Scheme 27
a) Synthesis of Aza-Bridged Lactams by Denzer and Ott; b) Synthesis of Bridged Lactam Precursors via Dearomatization of Quinazolines
Scheme 28
Scheme 28
Synthesis of Bridged Lactams via Heck Reaction by Grigg
Scheme 29
Scheme 29
Unsuccessful Synthesis of 1-Azabicyclo[3.2.1]oct-3-en-7-one via Heck Reaction by Grigg
Scheme 30
Scheme 30
Synthesis of Bridged Lactams via Tandem RCM-Heck Reaction by Grigg
Scheme 31
Scheme 31
Synthesis of Bridged Lactams via Heck Reaction by Paquette (please use double-column format for Scheme 31)
Scheme 32
Scheme 32
a) Synthesis of Bridged Lactams via Heck Reactionby Ribelin; b) Synthesis of Bridged Lactam Precursors via Tandem Ugi-RCM Reaction
Scheme 33
Scheme 33
Synthesis of Bridged Lactams via Type II Acyl Imino Diels-Alder Reaction by Shea
Scheme 34
Scheme 34
Proposed Mechanism for Diels-Alder Reaction of Acetoxyamides 141
Scheme 35
Scheme 35
Synthesis of Indole-1-azabicyclo[5.3.1]undecan-2-onesvia Witkop Photocyclization by Sundberg
Scheme 36
Scheme 36
Synthesis of Indole-1-azabicyclo[6.3.1]dodecan-2-ones via Witkop Photocyclization by Sundberg
Scheme 37
Scheme 37
Synthesis of Benzo-1-azabicyclo[4.2.1]nonan-2-one via Radical Cyclization by Hsung
Scheme 38
Scheme 38
Synthesis of 1-Azabicyclo[5.3.1]undecan-10-ones via Radical Fragmentation by Beckwith
Scheme 39
Scheme 39
Synthesis of Bridged Lactams via Friedel-Crafts Reaction by Ruchirawat
Scheme 40
Scheme 40
Synthesis of Indole-1-azabicyclo[6.2.2]dodecan-10-one via Fragmentation/Transannular Condensationby Dolby
Scheme 41
Scheme 41
Synthesis of 1-Azabicyclo[4.1.1]octan-7-onesvia Rh-Catalyzed N–H Insertion by Williams
Scheme 42
Scheme 42
Regiochemical Options in the Intramolecular Schmidt Reaction of 2-Alkylazido Ketones
Scheme 43
Scheme 43
Proposed Mechanism for Domino Diels-Alder/Schmidt Reaction of Keto-Azidotrienes 175 (please use double-column format for Scheme 43)
Scheme 44
Scheme 44
Synthesis of Bridged Lactams via Cation-π-Directed Schmidt Reaction by Aubé
Scheme 45
Scheme 45
Proposed Mechanism for Schmidt Reaction of 2-Aryl-2-Alkylazido Ketones 179
Scheme 46
Scheme 46
Synthesis of Bridged Lactams via Cation–n Directed Schmidt Reaction by Aubé
Scheme 47
Scheme 47
Proposed Mechanism for Schmidt Reaction of 2-Alkylazido Ketones 182
Scheme 48
Scheme 48
Other Examples of Bridged Lactams Synthesized via Intramolecular Schmidt Reaction
Scheme 49
Scheme 49
Synthesis of Indole-Derived Bridged Lactams via Transannular Amidation by Schill
Scheme 50
Scheme 50
Synthesis of Indole-Derived Bridged Lactams via Transannular Amide Coupling by Schill
Scheme 51
Scheme 51
a) Synthesis of 6-Phenyl-1-azabicyclo[4.3.1]decan-10-one by Magnus; b) Synthesis of Nine-Membered Ring Precursor
Scheme 52
Scheme 52
Synthesis of Bridged Lactam from Vincristine Metabolite by Dennison (please use double-column format for Scheme 52)
Scheme 53
Scheme 53
Synthesis of One-Carbon Bridged Lactamsvia Tandem RCM/Transannular Amidation by Aubé
Scheme 54
Scheme 54
Other Examples of Synthesis of One-Carbon Bridged Lactams via Condensation Reactions: a) 1-Azabicyclo[4.2.1]nonane-5,9-dione by Arata; b) 1-Azabicyclo[3.3.1]nonane-4,6,9-trione by Waly; c) 1-Azabicyclo[4.2.1]nonan-9-one by Smet
Scheme 55
Scheme 55
Synthesis of Benzo-4-thia-1-azabicyclo[3.2.1]octan-8-one 216 by Nazarenko
Scheme 56
Scheme 56
Synthesis of 1-Azabicyclo[6.2.1]undecan-11-one via RCM by Doodeman and Hiemstra
Scheme 57
Scheme 57
Synthesis of Chloro-Substituted Bridged Lactam via Aziridinium Rearrangement by Arata
Scheme 58
Scheme 58
Proposed Mechanism for Rearrangement of 224
Scheme 59
Scheme 59
Synthesis of 5,9,9-Trichloro-1-azabicyclo[3.3.1]nonane by Miyano
Scheme 60
Scheme 60
Synthesis of Bridged Lactams viaPhotolysis of Chloroacetamides by Bremner
Scheme 61
Scheme 61
Proposed Mechanism for Cyclization/Fragmentation of 230
Scheme 62
Scheme 62
Synthesis of 1-Azabicyclo[7.3.1]tridecan-13-onesvia Oxidation of Enamines by Schumann
Scheme 63
Scheme 63
Proposed Mechanism for Oxidation/Fragmentation of Enamines 232 and 232a
Scheme 64
Scheme 64
Synthesis of 1-Azabicyclo[6.2.1]undecan-11-one by Bailey
Scheme 65
Scheme 65
Proposed Mechanism for Oxidative Fragmentation of 236
Scheme 66
Scheme 66
Synthesis of Bridged Lactams via Rearrangement of Nitrogen Ylides by Rudler
Scheme 67
Scheme 67
Proposed Mechanism for Rearrangement of 239
Scheme 68
Scheme 68
Synthesis of 1,4-Bridged Pyrazolin-5-ones via Rearrangement of Spiro Pyrazolium Ylides by Chuche
Scheme 69
Scheme 69
Synthesis of Vinblastine-Derived Bridged Lactams by Kutney
Scheme 70
Scheme 70
Attempted Synthesis of 1-Azabicyclo[3.1.1]heptan-6-one by Williams
Scheme 71
Scheme 71
Attempted Synthesis of 1-Azabicyclo[3.2.1]octan-8-onesvia Amidoselenation by Toshimitsu
Scheme 72
Scheme 72
Synthesis of Tropane-Derived Bridged Lactams in Synthetic Studies towards Stemofoline by Thomas
Scheme 73
Scheme 73
a) Synthesis of Bridged Monothioimidevia Photochemical Fragmentation/Photocyclization by Sakamoto; b) Rearrangement of One-Carbon Higher Analog
Scheme 74
Scheme 74
Synthesis of Complex Bridged Imides via [2+2] Photocycloaddition by Booker-Milburn
Scheme 75
Scheme 75
Proposed Mechanism for Photocycloaddition of Imides 266 (please use double-column format for Scheme 75)
Scheme 76
Scheme 76
Synthesis of 3-Alkyl-1,3-diazabicyclo[3.3.1]nonan-2-ones by Hall
Scheme 77
Scheme 77
Synthesis of 1,3-diazabicyclo[3.3.1]nonan-2-ones by Hall
Scheme 78
Scheme 78
Synthesis of Bridged Urethanes by Hall: a) 3-Oxa-1-azabicyclo[3.3.1]nonan-2-one; b) 6-oxa-1-azabicyclo[3.2.1]octan-7-one
Scheme 79
Scheme 79
Synthesis of β-Lactamase Inhibitor Containing 1,6-Diazabicyclo[3.2.1]octan-7-one Scaffold by Mangion
Scheme 80
Scheme 80
Synthesis of Unsubstituted Bridged Oxazinolactams via Type II N-Acylnitroso Diels-Alder Reaction by Shea
Scheme 81
Scheme 81
Synthesis of Unsubstituted [6.2.1] Bridged Oxazinolactamvia Type II N-Acylnitroso Diels-Alder Reaction by Shea
Scheme 82
Scheme 82
Synthesis of Substituted Bridged Oxazinolactams via Type II N-Acylnitroso Diels-Alder Reaction by Shea
Scheme 83
Scheme 83
Synthesis of Bridged 1,2-Diazines via Type II N-Acylazo Diels-Alder Reaction by Shea
Scheme 84
Scheme 84
Asymmetric Synthesis Bridged Oxazinolactams via Dual Function Catalysis by Shea
Scheme 85
Scheme 85
Proposed Mechanism for Diels-Alder Reaction of Substrate 300
Scheme 86
Scheme 86
Early Attempts to Synthesize Bridged Lactams from Barbituric Acids by Smissman: a) Alkylation of 5-Iodoalkylbarbituric Acid; b) Electrophilic Activation of N-Allylbarbituric Acid; c) Alkylation of N-Haloalkylbarbituric Acid
Scheme 87
Scheme 87
Early Attempts to Synthesize Bridged Lactams from Amides and Imides by Smissman: a) Intramolecular Condensation; b) Intramolecular N-Alkylation
Scheme 88
Scheme 88
Revision of Initially Reported Structures of Bridged Barbituric Acids: a) Barbituric Acid 322 Reported by Meltzer and Lewis; b) Barbituric Acid 325 Reported by Baumler (please use double-column format for Scheme 88)
Scheme 89
Scheme 89
Synthesis of Bridged 2,4-Oxazolinediones by Brouillette
Scheme 90
Scheme 90
Synthesis of Bridged Hydantoines by Brouillette
Scheme 91
Scheme 91
Revision of Structure of Bridged Barbituric Acid Initially Reported by Smissman
Scheme 92
Scheme 92
Attempted Synthesis of Bridged Barbituric Acid by Gmünder and Lindenmann
Scheme 93
Scheme 93
a) Synthesis of 1-Azabicyclo[3.2.2]non-2-ene by Doering; b) Equilibrium between Bridged Allylic Amine and Enamine
Scheme 94
Scheme 94
Synthesis of Bridged Enamine via Au-Catalyzed Hydroamination by Funk
Scheme 95
Scheme 95
Synthesis of Bridged Bicyclic Enamines by Tandem Rh-Catalyzed C–H Activation/Alkenylation/Electrocyclization by Ellman
Scheme 96
Scheme 96
Proposed Mechanism for Synthesis of 352
Scheme 97
Scheme 97
Synthesis of Bridged Enamines viaIntramolecular Schmidt Reaction by Pearson
Scheme 98
Scheme 98
Proposed Mechanism for Schmidt Reaction of Azidoalkyl Alcohols
Scheme 99
Scheme 99
Generation of Bridged 1-Aza Iminium Ions by Hoffmann: a) Quinine Series; b) Quinidine Seires; c) Structures of Quinine and Quinidine
Scheme100
Scheme100
a) Synthesis of 1-Azabicyclo[3.3.1]nonanes by Miyano; b) Generation of Bridged Iminium Ions from 1-Azabicyclo[3.3.1]nonanes
Scheme 101
Scheme 101
Synthesis of Bridged Sultams via Heck Reaction by Grigg
Scheme 102
Scheme 102
Synthesis of Bridged Sultams via Heck Reaction by Paquette
Scheme 103
Scheme 103
Synthesis of Bridged Sultams via Tandem Heck Reaction/Hydrogenation by Evans
Scheme 104
Scheme 104
Synthesis of Bridged Sultams via Radical Cyclization by Paquette
Scheme 105
Scheme 105
Synthesis of Bridged Disulfonimide via Radical Cyclization by Paquette
Scheme 106
Scheme 106
a) Synthesis of “Apex” Bridged Sultam by Paquette; b) Unsuccessful Approach via RCM
Scheme 107
Scheme 107
Synthesis of Bridged Sultams via Double Alkylation by de Meijere
Scheme 108
Scheme 108
Synthesis of Benzofused Bridged Sultams via Sulfonylation/SNAr of Amino Alcohols by Hanson
Scheme 109
Scheme 109
Synthesis of Heteroatom-Derived Bridged Sultams via Rh-Catalyzed Allene Sulfamidation by Blakey
Scheme 110
Scheme 110
Proposed Mechanism for Synthesis of 407
Scheme 111
Scheme 111
a) Hydrolysisof 6,6-Dimethylquinuclidin-2-one; b) Hydrolysis of 6,6-Dimethyl-2-quinuclidinium Chloride by Pracejus
Scheme 112
Scheme 112
a) Hydrolysis of Benzo-2-quinuclidone by Blackburn; b) Hydrolysis of Extended Ring Systems of Benzo-2-quinuclidones by Brown
Scheme 113
Scheme 113
a) Hydrolysis of 1-Aza-2-adamantanone; b) Proposed Mechanismfor Hydrolysis by Kirby
Scheme 114
Scheme 114
Synthesis of 1-Aza-2-adamantanone from the Corresponding Amino Acid by Kirby
Scheme 115
Scheme 115
Hydrolysis of 2-Quinuclidonium Tetrafluoroborate by Stoltz
Scheme 116
Scheme 116
Hydrolysis of Medium Bridged Twisted Lactams by Aubé
Scheme 117
Scheme 117
Hydrolysis of Aza-Bridged Lactams by Denzer and Ott
Scheme 118
Scheme 118
Hydrolysis of 6-Chloro-1-Azabicyclo[4.4.1]undecan-11-one by Arata
Scheme 119
Scheme 119
N-Protonation and N-Methylation of 2-Quinuclidones by Pracejus and Yakhontov
Scheme 120
Scheme 120
N-Methylation and N-Protonation of 1-Aza-2-adamantanone by Kirby
Scheme 121
Scheme 121
N-Methylation vs. O-Methylation of Benzo-2-quinuclidones by Brown
Scheme 122
Scheme 122
N-Protonation vs. O-Protonation of 1-Azabicyclo[3.3.1]nonan-2-one by Greenberg
Scheme 123
Scheme 123
N-Protonation and N-Methylation of Medium Bridged Twisted Lactams by Aubé
Scheme 124
Scheme 124
Reactions of 6,6,7,7-Tetramethylquinuclidin-2-one with Cleavage of C–NC(O) Bond by Yakhontov
Scheme 125
Scheme 125
Proposed Mechanism for Synthesis of 436
Scheme 126
Scheme 126
Cleavage of C–NC(O) Bond in Medium-Bridged Twisted Lactams by Aubé: a) Amidinium Salts; b) Oxidative Cleavage
Scheme 127
Scheme 127
Hydrogenolysis of C–NC(O) Bond in Medium-Bridged Twisted Lactams by Aubé
Scheme 128
Scheme 128
a) Synthesis of Bridged Thioamide by Aubé; b) Proposed Mechanism Involving Cleavage of C–NC(S) Bond
Scheme 129
Scheme 129
Reduction of 6,6,7,7-Tetramethylquinuclidin-2-one by Yakhontov
Scheme 130
Scheme 130
Alcoholysis of 6,6-Dimethylquinuclidin-2-one by Pracejus
Scheme 131
Scheme 131
Aminolysis of [3.2.1] Bridged Lactam by Aszodi
Scheme 132
Scheme 132
Alcoholysis of One-Carbon Bridged Lactams by Murphy
Scheme 133
Scheme 133
Synthesis of Bridged Amino-Ketal from 1-Aza-2-adamantanone by Kirby
Scheme 134
Scheme 134
Synthesis and Reactions of Aminocarbene from 1-Aza-2-adamantanone by Kirby
Scheme 135
Scheme 135
Wolff-Kishner Reduction of Bridged Lactam by Coe
Scheme 136
Scheme 136
Proposed Mechanism for Synthesis of Bridged Amidine 462
Scheme 137
Scheme 137
Reactions of Medium-Bridged Twisted Lactams with Heteroatom Nucleophiles by Aubé
Scheme 138
Scheme 138
Reduction of 1,5-Diazabicyclo[3.3.1]nonan-2-one by Denzer and Ott
Scheme 139
Scheme 139
Reduction of Adamantane-Derived Bridged Lactam by Coe
Scheme 140
Scheme 140
Reduction of Medium-Bridged Twisted Lactams with Formation of Isolable Hemiaminals by Aubé
Scheme 141
Scheme 141
Reduction of Medium-Bridged Twisted Lactams with Collapse of Hemiaminals by Aubé
Scheme 142
Scheme 142
a) Reduction of Chloro-Substituted Bridged Lactam by Arata; b) Synthesis of 1-Azabicyclo[4.4.1]undecane
Scheme 143
Scheme 143
Proposed Mechanism for Rearrangement of 225
Scheme 144
Scheme 144
Reduction of Tropane-Derived Bridged Lactam by Thomas
Scheme 145
Scheme 145
Reduction of Bridged Lactams Derived from Amaryllidaceae Alkaloids by: a) Wildman; b) Hendrickson
Scheme 146
Scheme 146
Reduction of Indole-1-azabicyclo[6.2.2]dodecan-10-one by Dolby
Scheme 147
Scheme 147
Synthesis of Bridged Hemiaminal from Bridged Lactam by Harley-Mason
Scheme 148
Scheme 148
Corey-Chaykovsky Epoxidation of Bridged Lactams by Aubé
Scheme 149
Scheme 149
a) Wittig Olefination of 1-Aza-2-adamantanone by Kirby; b) Petasis Olefination of Medium Bridged Twisted Lactams by Aubé; c) Wittig Olefination of Tröger’s Base-Derived Twisted Lactams by Wärnmark
Scheme 150
Scheme 150
Cyanide-Induced Rearrangement of Indole-1-azabicyclo[6.3.1]dodecan-12-one by Ban
Scheme 151
Scheme 151
Proposed Mechanism for Cyanide-Induced Rearrangement of Lactam 498
Scheme 152
Scheme 152
α-Arylation of Indole-1-azabicyclo[5.4.1]dodecan-12-one by Schill
Scheme 153
Scheme 153
Rh-Catalyzed Conjugate Addition of Boronic Acid to 1-Azabicyclo[4.3.1]dec-7-en-9-one by Judd
Scheme 154
Scheme 154
Reactivity of 1-Azabicyclo[3.3.1]non-5-en-2-one Bearing Anti-Bredt Olefin by Shea
Scheme 155
Scheme 155
Synthesis of Bridged Lactams with Endocyclic Diene Motifs by Paquette
Scheme 156
Scheme 156
Photochemical Reactions of Bridged Lactams Bearing Endocyclic Dienes by Paquette
Scheme 157
Scheme 157
Reactivity of Bridged Oxazinolactamsby Shea: a) Reduction; b) Alkylation
Scheme 158
Scheme 158
Stereoselective Synthesis of Medium Ring Lactams from Oxazinolactams by Shea
Scheme 159
Scheme 159
Reactivity of Bridged 1,2-Diazines by Shea
Scheme 160
Scheme 160
Application of Bridged Oxazinolactams in Synthetic Studies towards Stenine by Shea (please use double-column format for Scheme 160)
Scheme 161
Scheme 161
a) N-Methylation of 3,5,7-Trimethyl-2-methylene-1-azaadamantane by Kirby; b) N-Protonation of 9-Methyl-9-Azabicyclo[3.3.1]non-1-ene by Kresge
Scheme 162
Scheme 162
Reactivity of Endocyclic [4.3.1] Bridged Enamines by Ellman
Scheme 163
Scheme 163
Reactivity of Bridged Enamines Prepared by Schmidt Reaction by Pearson: a) [3.2.2] Scaffold; b) [2.2.2] Scaffold
Scheme 164
Scheme 164
Alkylation and Oxidation of Bridged Sultams by Paquette
Scheme 165
Scheme 165
Bromination/Elimination of Bridged Sultams by Paquette
Scheme 166
Scheme 166
Bromination and Epoxidation of Benzo-Bridged Sultams by Evans
Scheme 167
Scheme 167
Proposed Mechanism for Synthesis of 544
Scheme 168
Scheme 168
Hydrogenation of Bridged Sultams by Evans
Scheme 169
Scheme 169
Photoinduced Cleavage of SO2–N Bond of Bridged Sultams by Paquette
Scheme 170
Scheme 170
Photoisomerization and Cycloaddition of Bridged Sultams by Paquette: a) Benzo[4.3.1] Ring System; b) [4.2.1] Ring System
Scheme 171
Scheme 171
Synthesis of Pyrrolidines via Double Reduction of Bridged Sultams by Evans
Scheme 172
Scheme 172
Total Synthesis of Mesembrane via Double Reduction of Bridged Sultams by Evans
Scheme 173
Scheme 173
Total Synthesis of Fawcettidine by Dake (please use double-column format for Scheme 173)
Scheme 174
Scheme 174
a) Total Synthesis of Communesin F by Ma; a) Total Synthesis of Communesins A and B by Ma (please use double-column format for Scheme 174)
Scheme 175
Scheme 175
a) Biomimetic Proposal for Synthesis of Communesins A and B by Stoltz; b) Biomimetic Proposal for Synthesis of Communesin B by Funk; c) Total Synthesis of Perophoramidine by Funk (please use double-column format for Scheme 175)
Scheme 176
Scheme 176
a) Approach to Cripowellin Aglycon by Moon; b) Synthesis of 1-epi-Aglycon of Cripowellins A nd B by Enders (please use double-column format for Scheme 176)
Scheme 177
Scheme 177
Synthesis of Mequitazine by Doris (please use double-column format for Scheme 177)
Scheme 178
Scheme 178
Synthesis of Indole Alkaloids by Harley-Mason: a) Tubifoline and Condyfoline; b) Geissoschizoline; c) Fluorocurarine; d) Condylocarpine (please use double-column format for Scheme 178)
Scheme 179
Scheme 179
Synthesis of Quebrachamine and 1,2-Dehydroaspidospermidine by Ban (please use double-column format for Scheme 179)
Scheme 180
Scheme 180
Synthesis of Indole Alkaloids via Friedel-Crafts Acylation of Bridged Amides: a) Quebrachamine by Ziegler and Bosch; b) Dihydrocleavamine by Bosch and Lesma; c) Tabersonine by Ziegler; d) Cleavamine by Hanaoka (please use double-column format for Scheme 180)
Scheme 181
Scheme 181
a) Application of Bridged Amide in Total Synthesis of Tubifoline by Bosch; b) Application in Bridged Amide in Total Synthesis of Strychnine by Magnus
Scheme 182
Scheme 182
Total Synthesis of Velbanamine: a) Büchi; b) Narisada (please use double-column format for Scheme 182)
Scheme 183
Scheme 183
Bridged Lactams in Total Synthesis of Amaryllidaceae Alkaloids: a) Oxohaemanthidine, Oxodihydrohaemanthidine, Oxoapohaemanthidine and Pretazzetine; b) Dihydrocrinine; c) 6,11-Dioxocrinene; d) Haemanthidine (please use double-column format for Scheme 183)
Scheme 184
Scheme 184
Total Synthesis of Kopsijasminilam by Magnus; b) Total Synthesis of and Pauciflorine B by Magnus; c) Total Synthesis of Kopsijasminilam by Kuehne (please use double-column format for Scheme 184)
Scheme 185
Scheme 185
Stemona Alkaloids Containing Bridged Amide Bonds (please use double-column format for Scheme 185)
Scheme 186
Scheme 186
Daphnum Alkaloids Containing Bridged Amide Bonds (please use double-column format for Scheme 186)
Scheme 187
Scheme 187
Indole Alkaloids Containing Bridged Amide Bonds (please use double-column format for Scheme 187)
Scheme 188
Scheme 188
Cripowellins Containing Bridged Amide Bonds (please use double-column format for Scheme 188)
Scheme 189
Scheme 189
Lycopodium Alkaloids Containing Bridged Amide Bonds (please use double-column format for Scheme 189)
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