C3–C4 THP-forming processes
retrosynthetic disconnections, 76, 77
ring-closing metathesis
class 1, 77–79
class 2, 79–80
ruthenium catalysts, 76, 77
C-disaccharide, 180, 181
Cephalosporolides E and F, 193
Cephalostatin 1, 228
C-glycoside, 169, 173
Chalconide and halide/metal exchange,
174–177
Chelate-controlled reduction, 87
Chiral acetonide dienophiles in
HDA reactions, 82, 83
Chiral auxilliary, 165, 168, 180
Chiral pheromone lactones, 110
(–)-Chlorothricolide, 413, 414
1,4-Cineole, 145–146
Cobalt catalyzed cyclization, 19
Coke and Richon synthesis, δ-lactones,
100, 101
(–)-Colletol, 417, 418
Combretastatins D, 422, 423
Condensation/hydride reduction sequence,
87, 88
Conduramine, 169, 170
Conduritol, 169, 171
Conformers, 190
Corey–Brunelle condition, 407, 408
Corey–Nicolaou method, 406
C ˇ oric ´ and List approach, 212
Cr(III)-catalyzed HDA reaction, 83, 84
Creticacumarin, 147
Cruentaren A, 374–375
Cycloaddition, tetrahydrofuran
allylsilane–aldehyde
chiral allylsilane, 15, 16
[3+2]-cycloadditions, 14, 15
lytophilippines, 18
mechanistic hypothesis, 15
triple allylation, 16
Trost’s two-step approach, 17, 18
cyclopropane–aldehyde
[3+2]-cycloadditions
amino cyclopropane, 10
cis-cyclopropanes, 10
diastereoselective, 10
enantioselective variant, 11
(+)-isatisine A, 12–13
(+)-polyanthellin A, 11–12
push–pull cyclopropanes, 9
Ru-allenylidene, 11
trans-cyclopropanes, 9
(+)-virgatusin, 12
oxonium ylide approach, 18
Prins cyclization, 13
Cyclophellitol, 168, 169
Cyclopropyl furans, 7
D
Danishefsky’s diene, 82, 83
Dehydrative spirocyclization, 194, 196
aliphatic spiroacetals
cephalosporolides E and F, 193
iron(0)-tricarbonyl diene
complex, 196
spirofungin A, 194
spongistatin-1, 194, 195
bis(benzannulated) spiroacetals
Ir/SpinPHOX catalysts, 200, 201
paecilospirone, 200
spirocyclization, 202–205
mono(benzannulated) spiroacetals
acortatarins, 199, 203
HWE/chemoselective reduction
strategy, 197, 198
HWE/deprotection strategy, 197, 198
Kulinkovich coupling/ring-opening
strategy, 197
6-Deoxyerythronolide B, 401
(+)-10-Deoxymethynolide, 397
Diazonamide A, 417, 418
Diels–Alder (DA) reaction, 81, 161–166
DIHMA. See Double intramolecular
hetero-Michael addition (DIHMA)
Dihydronepetalactone, 110, 111
Dihydroxy olefin cyclizations, 20
Dioxolenone, 386–387
Displacement cyclization strategies, 53, 54
Diterpenoid, 150–151
Double intramolecular hetero-Michael
addition (DIHMA), 232, 233
calyculin C, 233
dinemasone A, 233, 234
okadaic acid, 233
Dynemicin A, 413–414
E
Elaiolide, 395–396
Electron transfer initiated cyclization (ETIC)
method, 66, 67
Electrophilic cyclization, 228, 229, 295–298
cephalostatin 1, 228
Index
431
retrosynthetic disconnections, 76, 77
ring-closing metathesis
class 1, 77–79
class 2, 79–80
ruthenium catalysts, 76, 77
C-disaccharide, 180, 181
Cephalosporolides E and F, 193
Cephalostatin 1, 228
C-glycoside, 169, 173
Chalconide and halide/metal exchange,
174–177
Chelate-controlled reduction, 87
Chiral acetonide dienophiles in
HDA reactions, 82, 83
Chiral auxilliary, 165, 168, 180
Chiral pheromone lactones, 110
(–)-Chlorothricolide, 413, 414
1,4-Cineole, 145–146
Cobalt catalyzed cyclization, 19
Coke and Richon synthesis, δ-lactones,
100, 101
(–)-Colletol, 417, 418
Combretastatins D, 422, 423
Condensation/hydride reduction sequence,
87, 88
Conduramine, 169, 170
Conduritol, 169, 171
Conformers, 190
Corey–Brunelle condition, 407, 408
Corey–Nicolaou method, 406
C ˇ oric ´ and List approach, 212
Cr(III)-catalyzed HDA reaction, 83, 84
Creticacumarin, 147
Cruentaren A, 374–375
Cycloaddition, tetrahydrofuran
allylsilane–aldehyde
chiral allylsilane, 15, 16
[3+2]-cycloadditions, 14, 15
lytophilippines, 18
mechanistic hypothesis, 15
triple allylation, 16
Trost’s two-step approach, 17, 18
cyclopropane–aldehyde
[3+2]-cycloadditions
amino cyclopropane, 10
cis-cyclopropanes, 10
diastereoselective, 10
enantioselective variant, 11
(+)-isatisine A, 12–13
(+)-polyanthellin A, 11–12
push–pull cyclopropanes, 9
Ru-allenylidene, 11
trans-cyclopropanes, 9
(+)-virgatusin, 12
oxonium ylide approach, 18
Prins cyclization, 13
Cyclophellitol, 168, 169
Cyclopropyl furans, 7
D
Danishefsky’s diene, 82, 83
Dehydrative spirocyclization, 194, 196
aliphatic spiroacetals
cephalosporolides E and F, 193
iron(0)-tricarbonyl diene
complex, 196
spirofungin A, 194
spongistatin-1, 194, 195
bis(benzannulated) spiroacetals
Ir/SpinPHOX catalysts, 200, 201
paecilospirone, 200
spirocyclization, 202–205
mono(benzannulated) spiroacetals
acortatarins, 199, 203
HWE/chemoselective reduction
strategy, 197, 198
HWE/deprotection strategy, 197, 198
Kulinkovich coupling/ring-opening
strategy, 197
6-Deoxyerythronolide B, 401
(+)-10-Deoxymethynolide, 397
Diazonamide A, 417, 418
Diels–Alder (DA) reaction, 81, 161–166
DIHMA. See Double intramolecular
hetero-Michael addition (DIHMA)
Dihydronepetalactone, 110, 111
Dihydroxy olefin cyclizations, 20
Dioxolenone, 386–387
Displacement cyclization strategies, 53, 54
Diterpenoid, 150–151
Double intramolecular hetero-Michael
addition (DIHMA), 232, 233
calyculin C, 233
dinemasone A, 233, 234
okadaic acid, 233
Dynemicin A, 413–414
E
Elaiolide, 395–396
Electron transfer initiated cyclization (ETIC)
method, 66, 67
Electrophilic cyclization, 228, 229, 295–298
cephalostatin 1, 228
Index
431