14-member, 383–384
15-member, 384
16-member, 384–385
Ring expansion and rearrangement
advantages, 355
cyclopropanes, 356
five-membered ethers, 356–359
Ring lactones. See 12-to 16-membered-ring
lactones
Ring-opening metathesis (ROM)
enyne metathesis, 29, 30, 32
fused tetrahydrofurans, 29, 31
glutamate ligands, 31, 34
optically active 7-oxanorbornenes, 32, 34
phelligridin G scaffold, 32, 34
regioselective reactions, 30, 33–34
spiro-fused tetrahydrofurans, 29, 31
Ruthenium catalyzed cyclizations, 20–21
S
Salicylaldehyde and ethyl chloroacetate,
287, 288
Salicylihalamides, 382, 391
Selenolactonization, 124–125
Sesquiterpenoid, 147–150
Seven-membered ring ethers
C–C bonds formation
anionic cyclization, 298–300
electrophilic cyclization, 295–298
metal-induced cyclization, 300–306
photochemical processes, 310–311
radical reactions, 307–310
thermal cycloadditions and
rearrangements, 306–307
C–O bond formation
epoxides ring opening, 291–292
hydroxyl ketones, reductive cyclization,
292–293
oxa-Michael reactions, 294–295
oxygenated nucleophiles, 288–291
polyenes oxidation, 291–292
Ullmann coupling, 293–294
oxygenated structures, ring expansion
bicyclo[4.1.0] heptanes,
cyclopropanation and ring opening,
284–286
2-halomethyl cyclic ethers, 289
4-methylene-chromanes, 287, 288
pyranones, Arndt–Eistert reaction,
286–287
salicylaldehyde and ethyl chloroacetate,
287, 288
Seven-membered ring lactones
halolactonisation, 313
ω-hydroxy acids lactonisation, 313–314
oxidative processes, 311–313
ring enlargement, 314–316
tandem Suzuki coupling/
macrolactonisation, 314
Six-membered ring lactones
γ-acyl-δ-lactones, 135
alduronic acid lactones, 134, 135
Baeyer–Villiger oxidation
δ-lactones, 115–116
optically active δ-lactones, 116
Prelog–Djerassi lactone, 114–115
biological importance, 99
carbonylation, 129–130
carboxylation, 130–131
halolactonization, 124–125
1-hydroperoxy-2-oxabicycloalkanes, 136
integerrinecic acid lactone, 131–132
intramolecular Claisen-type condensation,
132, 133
intramolecular nucleophilic
displacement, 126
lactol oxidation
direct catalytic enantioselective
synthesis, 123, 124
Huet and Robin synthesis, 120
(R)-mevalonolactone, 121, 122
Prelog–Djerassi lactonic acid, 120, 121
Yus and Ramo ´n synthesis, 119–120
lactonization
5-amino-δ-lactones, 105
argentilactone, 103
3-aryl-δ-lactones, 108–109
chiral pheromone lactones, 109
Corey–Bakshi–Shibata reduction, 105
diastereoselective synthesis, 103, 104
dihydronepetalactone, 110, 111
enantioselective Henry reaction, 113
(R)-(+)-5-hexadecanolide, 102
β-hydroxy δ-lactones, 103, 104
integerrinecic acid lactone, 103, 104
(–)-iridolactone, 108, 109
δ-lactones, 99–102
mevinic acid, 106
(+)-prelactone B, 114
Prelog–Djerassi lactonic acid, 108
ricciocarpins A and B, 110–111
4,5-substituted δ-lactones, 103, 104
tetrasubstituted δ-lactones, 106, 107
mevinic acid, 134
natural products, 98–99
Index
437
15-member, 384
16-member, 384–385
Ring expansion and rearrangement
advantages, 355
cyclopropanes, 356
five-membered ethers, 356–359
Ring lactones. See 12-to 16-membered-ring
lactones
Ring-opening metathesis (ROM)
enyne metathesis, 29, 30, 32
fused tetrahydrofurans, 29, 31
glutamate ligands, 31, 34
optically active 7-oxanorbornenes, 32, 34
phelligridin G scaffold, 32, 34
regioselective reactions, 30, 33–34
spiro-fused tetrahydrofurans, 29, 31
Ruthenium catalyzed cyclizations, 20–21
S
Salicylaldehyde and ethyl chloroacetate,
287, 288
Salicylihalamides, 382, 391
Selenolactonization, 124–125
Sesquiterpenoid, 147–150
Seven-membered ring ethers
C–C bonds formation
anionic cyclization, 298–300
electrophilic cyclization, 295–298
metal-induced cyclization, 300–306
photochemical processes, 310–311
radical reactions, 307–310
thermal cycloadditions and
rearrangements, 306–307
C–O bond formation
epoxides ring opening, 291–292
hydroxyl ketones, reductive cyclization,
292–293
oxa-Michael reactions, 294–295
oxygenated nucleophiles, 288–291
polyenes oxidation, 291–292
Ullmann coupling, 293–294
oxygenated structures, ring expansion
bicyclo[4.1.0] heptanes,
cyclopropanation and ring opening,
284–286
2-halomethyl cyclic ethers, 289
4-methylene-chromanes, 287, 288
pyranones, Arndt–Eistert reaction,
286–287
salicylaldehyde and ethyl chloroacetate,
287, 288
Seven-membered ring lactones
halolactonisation, 313
ω-hydroxy acids lactonisation, 313–314
oxidative processes, 311–313
ring enlargement, 314–316
tandem Suzuki coupling/
macrolactonisation, 314
Six-membered ring lactones
γ-acyl-δ-lactones, 135
alduronic acid lactones, 134, 135
Baeyer–Villiger oxidation
δ-lactones, 115–116
optically active δ-lactones, 116
Prelog–Djerassi lactone, 114–115
biological importance, 99
carbonylation, 129–130
carboxylation, 130–131
halolactonization, 124–125
1-hydroperoxy-2-oxabicycloalkanes, 136
integerrinecic acid lactone, 131–132
intramolecular Claisen-type condensation,
132, 133
intramolecular nucleophilic
displacement, 126
lactol oxidation
direct catalytic enantioselective
synthesis, 123, 124
Huet and Robin synthesis, 120
(R)-mevalonolactone, 121, 122
Prelog–Djerassi lactonic acid, 120, 121
Yus and Ramo ´n synthesis, 119–120
lactonization
5-amino-δ-lactones, 105
argentilactone, 103
3-aryl-δ-lactones, 108–109
chiral pheromone lactones, 109
Corey–Bakshi–Shibata reduction, 105
diastereoselective synthesis, 103, 104
dihydronepetalactone, 110, 111
enantioselective Henry reaction, 113
(R)-(+)-5-hexadecanolide, 102
β-hydroxy δ-lactones, 103, 104
integerrinecic acid lactone, 103, 104
(–)-iridolactone, 108, 109
δ-lactones, 99–102
mevinic acid, 106
(+)-prelactone B, 114
Prelog–Djerassi lactonic acid, 108
ricciocarpins A and B, 110–111
4,5-substituted δ-lactones, 103, 104
tetrasubstituted δ-lactones, 106, 107
mevinic acid, 134
natural products, 98–99
Index
437