Danishefsky’s diene, 82, 83
Ru-catalyzed tandem, 84, 85
Heterolysis, 171
Heterolytic cyclopropane ring-opening
strategy, 6
Hexoses, 169
Homolytic cyclopropane ring-opening
strategy, 7
Horner–Wadsworth–Emmons reaction, 107
(–)-Hybridalactone, 408
ω-Hydroxy acids lactonisation, 313
Hydroxyl ketones, reductive cyclization, 292
Hypothemycin, 422
I
Idea leuconoe, 109, 110
Illudin, 171
Imide, 145
Iminoalditols, 180
Indium(III)-promoted Prins cyclization, 68
Integerrinecic acid lactone, 103, 104
Integramycin model, 228, 229
Intramolecular Claisen-type condensation,
132, 133
Intramolecular hydrogen abstraction, 247–249
bis(benzannulated) spiroacetals, 250, 251
cryptoacetalide and
danshenspiroketallactone, 250, 251
hippuristanol, 249
γ-rubromycin, 252
(benzannulated) 5,5-spiroacetals, 252, 253
transition states, 249
Intramolecular nitrile oxide–olefin
cycloaddition (INOC)
description, 399
16-membered macrocyclic lactones, 400
Intramolecular nucleophilic displacement, 126
Intramolecular oxymercuration, 214
Invictolide, 126
Iodoetherification, 25, 26, 215, 217
Isoavenaciolide, 178, 179
Isolaurepan, 316–317
K
Keto-β-lactone cyclization, 4
Ketyl radical-anion, 172, 173
L
Lactimidomycin, 375–376
Lactones
formation, 385–386
to oxepins and oxepenes
acetylaranotin, 316–317
caprolactone, enol phosphate, 319
isolaurepan, 316–317
seven-membered ring (see
Seven-membered ring lactones)
six-membered ring
γ-acyl-δ-lactones, 135
alduronic acid lactones, 134, 135
Baeyer–Villiger oxidation, 114–117
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, 119–124
lactonization (see Six-membered ring
lactones, lactonization)
mevinic acid, 134
natural products, 98–99
N-heterocyclic carbene-catalyzed ring
expansion, 136
one-carbon ring enlargement, 134
one-step spiroannelation, 131
oxidative lactonization, 117–119
palladium-catalyzed lactonization,
128–129
radical cyclization, 127
samarium iodide-mediated reductive
cyclization, 127–128
selenolactonization, 124–125
Watt synthesis, 131, 132
12-to 16-membered-ring (see 12-to
16-membered-ring lactones)
Latrunculin A, 380, 381
(+)-Laurencin, 325, 326
(+)-Lepicidin A, 401–402
Leucascandrolide A, 404
chelate-controlled reduction, 87
late-stage a ring assembly, 48
14-membered macrocyclic lactones, 404
nucleophilic substitution approach, 53
Pd-catalyzed alkoxycarbonylation, 57
Prins cyclization strategies, 66–68
selenium-mediated alkene cyclization, 58
Lignan natural products, 2–3
Lonomycin A, 420, 421
Index
433
Ru-catalyzed tandem, 84, 85
Heterolysis, 171
Heterolytic cyclopropane ring-opening
strategy, 6
Hexoses, 169
Homolytic cyclopropane ring-opening
strategy, 7
Horner–Wadsworth–Emmons reaction, 107
(–)-Hybridalactone, 408
ω-Hydroxy acids lactonisation, 313
Hydroxyl ketones, reductive cyclization, 292
Hypothemycin, 422
I
Idea leuconoe, 109, 110
Illudin, 171
Imide, 145
Iminoalditols, 180
Indium(III)-promoted Prins cyclization, 68
Integerrinecic acid lactone, 103, 104
Integramycin model, 228, 229
Intramolecular Claisen-type condensation,
132, 133
Intramolecular hydrogen abstraction, 247–249
bis(benzannulated) spiroacetals, 250, 251
cryptoacetalide and
danshenspiroketallactone, 250, 251
hippuristanol, 249
γ-rubromycin, 252
(benzannulated) 5,5-spiroacetals, 252, 253
transition states, 249
Intramolecular nitrile oxide–olefin
cycloaddition (INOC)
description, 399
16-membered macrocyclic lactones, 400
Intramolecular nucleophilic displacement, 126
Intramolecular oxymercuration, 214
Invictolide, 126
Iodoetherification, 25, 26, 215, 217
Isoavenaciolide, 178, 179
Isolaurepan, 316–317
K
Keto-β-lactone cyclization, 4
Ketyl radical-anion, 172, 173
L
Lactimidomycin, 375–376
Lactones
formation, 385–386
to oxepins and oxepenes
acetylaranotin, 316–317
caprolactone, enol phosphate, 319
isolaurepan, 316–317
seven-membered ring (see
Seven-membered ring lactones)
six-membered ring
γ-acyl-δ-lactones, 135
alduronic acid lactones, 134, 135
Baeyer–Villiger oxidation, 114–117
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, 119–124
lactonization (see Six-membered ring
lactones, lactonization)
mevinic acid, 134
natural products, 98–99
N-heterocyclic carbene-catalyzed ring
expansion, 136
one-carbon ring enlargement, 134
one-step spiroannelation, 131
oxidative lactonization, 117–119
palladium-catalyzed lactonization,
128–129
radical cyclization, 127
samarium iodide-mediated reductive
cyclization, 127–128
selenolactonization, 124–125
Watt synthesis, 131, 132
12-to 16-membered-ring (see 12-to
16-membered-ring lactones)
Latrunculin A, 380, 381
(+)-Laurencin, 325, 326
(+)-Lepicidin A, 401–402
Leucascandrolide A, 404
chelate-controlled reduction, 87
late-stage a ring assembly, 48
14-membered macrocyclic lactones, 404
nucleophilic substitution approach, 53
Pd-catalyzed alkoxycarbonylation, 57
Prins cyclization strategies, 66–68
selenium-mediated alkene cyclization, 58
Lignan natural products, 2–3
Lonomycin A, 420, 421
Index
433