Tetrahydropyrans (THP) synthesis (cont.)
O1–C2 THP-forming processes
alkene-mediated cyclizations, 56–59
conjugate addition, 46–52
nucleophilic substitution cyclizations
(See Nucleophilic substitution
cyclization, tetrahydropyrans)
Thioester macrolactonization
Corey–Nicolaou method, 406
description, 405
double activation, 405
macrocyclic lactones
12-member, 406–407
13-member, 408
14-member, 408, 409
16-member, 408, 409
Tokuyama’s synthesis, 318
Transition metal-catalyzed intramolecular
hydroalkoxylation approach,
215, 217
aliphatic bis(spiroacetals), 222
aliphatic spiroacetals
1,3-anti and 1,3-syn propargylic
triols, 219
Au(I)-catalyzed hydroalkoxylation
approah, 218
cephalosporolide E, 220, 221
enantiomeric cephalosporolides,
220, 222
Hg(II)-catalyzed hydroalkoxylation,
222, 223
okadaic acid, 219, 220
ushikulide A, 219, 221
bis(benzannulated) spiroacetals, 225–228
internal alkynes, 215
mono(benzannulated) spiroacetals
gold(I)-catalyzed synthesis, 224
Hg(II)-catalyzed synthesis, 225, 227
internal alkynes, 224, 226
Rh(I)-and Ir(I)-based catalysts,
224, 225
Pd-catalyzed, 217
Triterpenoid, 153–158
Tujinpi, 98
12-to 16-membered-ring lactones
alkyl alkynyl ethers, ketene source,
385–386
late-stage C–H oxidative
macrolactonization, intramolecular,
400–401
macrolactones
benzodioxinones to benzolactones,
390–391
intramolecular capture, acylketenes,
386–390
nitrile oxide–olefin cycloaddition,
intramolecular, 399–400
Nozaki–Hiyama–Kishi coupling
strategy, 396–399
Stille and Stille-type transformations,
394–396
Wittig and HWE transformations,
392–395
Yamamoto vinylogous aldol reaction,
391–393
Mitsunobu reaction, 420–423
Mukaiyama macrolactonization, 409–412
phosphorus-based reagents
macrolactonization, 412–416
ring-closing alkyne metathesis, 372–380
ring-closing olefin metathesis, 380–385
Steglich and Boden–Keck variants, 416–419
thioesters macrolactonization, 405–409
Yamaguchi macrolactonization, 401–405
U
Ullmann coupling, 293–294
Uronolactone, 180
W
Wacker-type cyclization, 257
White and Jayasinghe synthesis, of
integerrinecic acid lactone, 103, 104
Wittig and HWE transformations
12-membered macrocyclic lactones,
392–394
14-membered macrocyclic lactones, 394
16-membered macrocyclic lactones,
394–395
Woerpel’s model, 2
Y
Yamaguchi macrolactonization
description, 401
macrocyclic lactones
12-member, 401–402
13-member, 402–403
440
Index
O1–C2 THP-forming processes
alkene-mediated cyclizations, 56–59
conjugate addition, 46–52
nucleophilic substitution cyclizations
(See Nucleophilic substitution
cyclization, tetrahydropyrans)
Thioester macrolactonization
Corey–Nicolaou method, 406
description, 405
double activation, 405
macrocyclic lactones
12-member, 406–407
13-member, 408
14-member, 408, 409
16-member, 408, 409
Tokuyama’s synthesis, 318
Transition metal-catalyzed intramolecular
hydroalkoxylation approach,
215, 217
aliphatic bis(spiroacetals), 222
aliphatic spiroacetals
1,3-anti and 1,3-syn propargylic
triols, 219
Au(I)-catalyzed hydroalkoxylation
approah, 218
cephalosporolide E, 220, 221
enantiomeric cephalosporolides,
220, 222
Hg(II)-catalyzed hydroalkoxylation,
222, 223
okadaic acid, 219, 220
ushikulide A, 219, 221
bis(benzannulated) spiroacetals, 225–228
internal alkynes, 215
mono(benzannulated) spiroacetals
gold(I)-catalyzed synthesis, 224
Hg(II)-catalyzed synthesis, 225, 227
internal alkynes, 224, 226
Rh(I)-and Ir(I)-based catalysts,
224, 225
Pd-catalyzed, 217
Triterpenoid, 153–158
Tujinpi, 98
12-to 16-membered-ring lactones
alkyl alkynyl ethers, ketene source,
385–386
late-stage C–H oxidative
macrolactonization, intramolecular,
400–401
macrolactones
benzodioxinones to benzolactones,
390–391
intramolecular capture, acylketenes,
386–390
nitrile oxide–olefin cycloaddition,
intramolecular, 399–400
Nozaki–Hiyama–Kishi coupling
strategy, 396–399
Stille and Stille-type transformations,
394–396
Wittig and HWE transformations,
392–395
Yamamoto vinylogous aldol reaction,
391–393
Mitsunobu reaction, 420–423
Mukaiyama macrolactonization, 409–412
phosphorus-based reagents
macrolactonization, 412–416
ring-closing alkyne metathesis, 372–380
ring-closing olefin metathesis, 380–385
Steglich and Boden–Keck variants, 416–419
thioesters macrolactonization, 405–409
Yamaguchi macrolactonization, 401–405
U
Ullmann coupling, 293–294
Uronolactone, 180
W
Wacker-type cyclization, 257
White and Jayasinghe synthesis, of
integerrinecic acid lactone, 103, 104
Wittig and HWE transformations
12-membered macrocyclic lactones,
392–394
14-membered macrocyclic lactones, 394
16-membered macrocyclic lactones,
394–395
Woerpel’s model, 2
Y
Yamaguchi macrolactonization
description, 401
macrocyclic lactones
12-member, 401–402
13-member, 402–403
440
Index