Oxygenated structures (cont.)
salicylaldehyde and ethyl chloroacetate,
287, 288
Oxymercuration approach, 56
P
Palasonin, 144
Palladium catalyzed reactions
alkoxycarbonylation, 57, 59
cyclizations, 19, 20
desymmetrization, 57, 58
lactonization, 128–129
Pamamycin-607, 418–419
Panek [4+2]-annulation, tetrahydropyrans
2,6-cis DHPs, 74
leucascandrolide A, 74, 75
(+)-SCH 351448, 75
stereoselective annulation method,
73, 74
Pappo and Jung synthesis, δ-lactones, 101
Paterson and Khan synthesis, δ-lactones, 101
(+)-Patulolide A, 392–394
Peduncularine, 174–175
(+)-Peloruside A, 392, 393, 405, 406
Petasis–Ferrier union/rearrangement,
tetrahydropyrans
mechanism of, 71
phorboxazole A, 72
spongistatin 1, 73
trisubstituted alkenes, 71, 72
PGE 2 -1,15-lactone, 376–377
PGF 2α -1,15-lactone, 410, 411
Phosphatase inhibitors, 144
Phosphorus-based reagents
description, 412, 413
macrocyclic lactones
14-member, 413, 414
15-member, 413–414
16-member, 415
Photochemical processes, 310–311
Photo-induced reduction, 179
Pinacolic rearrangement, 163, 169
Polyenes oxidation, 291–292
(+)-Prelaureatin, 326, 328
Prelog–Djerassi lactonic acid, 108
Prins cyclization strategies, tetrahydropyrans
alkene geometry, 64, 65
allylic 1,2-diols in, 65
bryostatin 9, 69
diastereoselective nucleophilic trapping,
62, 63
leucascandrolide A, 65–67
phorboxazole B, 70
potential pathways, 63, 64
(+)-SCH 351488, 67, 68
Prins-pinacol cascades, 27–28
Prostaglandin, 152, 153
Pyranones, Arndt–Eistert reaction, 286, 287
R
rac-farnesiferol-C, 148, 149
Radical reactions, 127, 307–310
(+)-Rhizoxin D, 394–395
Rhodium-catalyzed hydrogenation, 78
Ricciocarpins A and B, 111, 112
Ring-closing alkyne metathesis (RCAM)
Cummins’ trisamidomolybdenum
complex 4, 372
description, 372
gem-dihalides usage, 372–373
12-membered macrocyclic lactones
cruentaren A, 374–375
lactimidomycin, 375–376
13-membered macrocyclic lactones,
376–377
14-membered macrocyclic lactones,
377, 378
15-membered macrocyclic lactones,
377–378
16-membered macrocyclic lactones
epothilones, 378–380
latrunculin A, 380, 381
metal complexes used in, 372–373
molybdenum trisamido complex 4, 373
Mortreux’s instant catalyst, 372
quantum leap, 372
Schrock alkylidyne complex 8, 374
tungsten alkylidyne complex 2, 372
Ring-closing metathesis (RCM), 254, 255
aigialospirol, 255
bis(spiroacetals), 255, 256
class 1
bryostatins, 79
(+)-SCH 351448, 78
stereoselective synthesis, 77, 78
class 2
leucascandrolide A, 79, 80
phorboxazoles, 79, 80
papulacandin-like spiroacetals, 255
Ring-closing olefin metatheses
description, 380–381
macrocyclic lactones
12-member, 382
13-member, 383
436
Index
salicylaldehyde and ethyl chloroacetate,
287, 288
Oxymercuration approach, 56
P
Palasonin, 144
Palladium catalyzed reactions
alkoxycarbonylation, 57, 59
cyclizations, 19, 20
desymmetrization, 57, 58
lactonization, 128–129
Pamamycin-607, 418–419
Panek [4+2]-annulation, tetrahydropyrans
2,6-cis DHPs, 74
leucascandrolide A, 74, 75
(+)-SCH 351448, 75
stereoselective annulation method,
73, 74
Pappo and Jung synthesis, δ-lactones, 101
Paterson and Khan synthesis, δ-lactones, 101
(+)-Patulolide A, 392–394
Peduncularine, 174–175
(+)-Peloruside A, 392, 393, 405, 406
Petasis–Ferrier union/rearrangement,
tetrahydropyrans
mechanism of, 71
phorboxazole A, 72
spongistatin 1, 73
trisubstituted alkenes, 71, 72
PGE 2 -1,15-lactone, 376–377
PGF 2α -1,15-lactone, 410, 411
Phosphatase inhibitors, 144
Phosphorus-based reagents
description, 412, 413
macrocyclic lactones
14-member, 413, 414
15-member, 413–414
16-member, 415
Photochemical processes, 310–311
Photo-induced reduction, 179
Pinacolic rearrangement, 163, 169
Polyenes oxidation, 291–292
(+)-Prelaureatin, 326, 328
Prelog–Djerassi lactonic acid, 108
Prins cyclization strategies, tetrahydropyrans
alkene geometry, 64, 65
allylic 1,2-diols in, 65
bryostatin 9, 69
diastereoselective nucleophilic trapping,
62, 63
leucascandrolide A, 65–67
phorboxazole B, 70
potential pathways, 63, 64
(+)-SCH 351488, 67, 68
Prins-pinacol cascades, 27–28
Prostaglandin, 152, 153
Pyranones, Arndt–Eistert reaction, 286, 287
R
rac-farnesiferol-C, 148, 149
Radical reactions, 127, 307–310
(+)-Rhizoxin D, 394–395
Rhodium-catalyzed hydrogenation, 78
Ricciocarpins A and B, 111, 112
Ring-closing alkyne metathesis (RCAM)
Cummins’ trisamidomolybdenum
complex 4, 372
description, 372
gem-dihalides usage, 372–373
12-membered macrocyclic lactones
cruentaren A, 374–375
lactimidomycin, 375–376
13-membered macrocyclic lactones,
376–377
14-membered macrocyclic lactones,
377, 378
15-membered macrocyclic lactones,
377–378
16-membered macrocyclic lactones
epothilones, 378–380
latrunculin A, 380, 381
metal complexes used in, 372–373
molybdenum trisamido complex 4, 373
Mortreux’s instant catalyst, 372
quantum leap, 372
Schrock alkylidyne complex 8, 374
tungsten alkylidyne complex 2, 372
Ring-closing metathesis (RCM), 254, 255
aigialospirol, 255
bis(spiroacetals), 255, 256
class 1
bryostatins, 79
(+)-SCH 351448, 78
stereoselective synthesis, 77, 78
class 2
leucascandrolide A, 79, 80
phorboxazoles, 79, 80
papulacandin-like spiroacetals, 255
Ring-closing olefin metatheses
description, 380–381
macrocyclic lactones
12-member, 382
13-member, 383
436
Index