M
Macrolactones
acylketenes, intramolecular capture,
386–390
benzodioxinones to benzolactones,
390–391
intramolecular nitrile oxide–olefin
cycloaddition, 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
Macrolactonization
Mukaiyama, 409–412
phosphorus-based reagents, 412–416
thioesters, 405–409
Yamaguchi, 401–405
(+)-Macrosphelide A, 408, 409
(+)-Macrosphelide B, 400
Maneonene, 149, 150
Manganese-mediated cyclizations, 21–23
Metal-induced cyclizations, 300–306
4-Methylene-chromanes, 287, 288
Methyl nonactate, 178
Michael-type cyclization, 50
Microbial approach, tetrahydrofuran, 28, 30
(+)-Migrastatin, 383–384
Mitsunobu reaction
description, 420, 421
macrocyclic lactones
12-member, 420, 421
13-member, 420, 421
14-member, 422
15-member, 422, 423
16-member, 422–423
Molecular device, 161, 162
Mono(benzannulated) spiroacetals
acortatarins, 199
HWE/chemoselective reduction strategy,
197, 198
HWE/deprotection strategy, 197, 198
Kulinkovich coupling/ring-opening
strategy, 197
Monoterpenoid, 145–147
Mukaiyama Aldol-Prins (MAP) method, 66, 67
Mukaiyama macrolactonization
description, 409–410
macrocyclic lactones
13-member, 410, 411
14-member, 410–411
16-member, 411, 412
principles, 410
N
Naked sugars, 168, 171, 180, 181
Narbonolide, 398
Natural 7-oxanorbornanes. See 7-Oxabicyclo
[2.2.1]heptane
Ni-catalyzed reductive cyclization
approach, 254
Nonactin, 178
Non-anomeric conformers, 190
Non-Diels–Alder approaches, 159–161
Norcantharidin, 144, 145
Norzoanthamine, 388, 389
Nozaki–Hiyama–Kishi (NHK) coupling
strategy
description, 396
macrocyclic lactones
12-member, 397
13-member, 397–398
14-member, 398
16-member, 398–399
Nucleophilic substitutions
tetrahydrofuran
2-alkylidene tetrahydrofuran, 33, 35
π-allyl cyclizations, 34, 36
asymmetric Horner–Wadsworth–
Emmons reaction, 38
epibromohydrin approach, 33, 36
halocyclization, 35, 37
Pd-catalyzed π-allyl cyclizations, 34, 36
Tandem Michael additions, 36, 38
tetrahydropyrans, cyclization
epoxide opening, 59–61
leucascandrolide A, 53
mechanistic considerations, 52, 53
phorboxazole A, 54, 55
phorboxazoles, 54, 55
spongistatin 1, 53, 54
O
O1–C2 THP-forming processes
alkene-mediated cyclizations
bryostatins, 56, 57
leucascandrolide A, 56–58
phorboxazoles, 57–59
stereochemical outcomes, 56, 57
conjugate addition
bond formation, 46, 47
434
Index
Macrolactones
acylketenes, intramolecular capture,
386–390
benzodioxinones to benzolactones,
390–391
intramolecular nitrile oxide–olefin
cycloaddition, 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
Macrolactonization
Mukaiyama, 409–412
phosphorus-based reagents, 412–416
thioesters, 405–409
Yamaguchi, 401–405
(+)-Macrosphelide A, 408, 409
(+)-Macrosphelide B, 400
Maneonene, 149, 150
Manganese-mediated cyclizations, 21–23
Metal-induced cyclizations, 300–306
4-Methylene-chromanes, 287, 288
Methyl nonactate, 178
Michael-type cyclization, 50
Microbial approach, tetrahydrofuran, 28, 30
(+)-Migrastatin, 383–384
Mitsunobu reaction
description, 420, 421
macrocyclic lactones
12-member, 420, 421
13-member, 420, 421
14-member, 422
15-member, 422, 423
16-member, 422–423
Molecular device, 161, 162
Mono(benzannulated) spiroacetals
acortatarins, 199
HWE/chemoselective reduction strategy,
197, 198
HWE/deprotection strategy, 197, 198
Kulinkovich coupling/ring-opening
strategy, 197
Monoterpenoid, 145–147
Mukaiyama Aldol-Prins (MAP) method, 66, 67
Mukaiyama macrolactonization
description, 409–410
macrocyclic lactones
13-member, 410, 411
14-member, 410–411
16-member, 411, 412
principles, 410
N
Naked sugars, 168, 171, 180, 181
Narbonolide, 398
Natural 7-oxanorbornanes. See 7-Oxabicyclo
[2.2.1]heptane
Ni-catalyzed reductive cyclization
approach, 254
Nonactin, 178
Non-anomeric conformers, 190
Non-Diels–Alder approaches, 159–161
Norcantharidin, 144, 145
Norzoanthamine, 388, 389
Nozaki–Hiyama–Kishi (NHK) coupling
strategy
description, 396
macrocyclic lactones
12-member, 397
13-member, 397–398
14-member, 398
16-member, 398–399
Nucleophilic substitutions
tetrahydrofuran
2-alkylidene tetrahydrofuran, 33, 35
π-allyl cyclizations, 34, 36
asymmetric Horner–Wadsworth–
Emmons reaction, 38
epibromohydrin approach, 33, 36
halocyclization, 35, 37
Pd-catalyzed π-allyl cyclizations, 34, 36
Tandem Michael additions, 36, 38
tetrahydropyrans, cyclization
epoxide opening, 59–61
leucascandrolide A, 53
mechanistic considerations, 52, 53
phorboxazole A, 54, 55
phorboxazoles, 54, 55
spongistatin 1, 53, 54
O
O1–C2 THP-forming processes
alkene-mediated cyclizations
bryostatins, 56, 57
leucascandrolide A, 56–58
phorboxazoles, 57–59
stereochemical outcomes, 56, 57
conjugate addition
bond formation, 46, 47
434
Index