mono(benzannulated) spiroacetals,
224–225
Pd-catalyzed, 217
Wacker-type cyclization, 257
(–)-Spongidepsin, 383
Spongistatin-1, 194, 195
Steglich and Boden–Keck variants
Boden–Keck protocol, 417
description, 416
macrocyclic lactones
12-member, 417
13-member, 417, 418
14-member, 417, 418
15-member, 418, 419
16-member, 418–419
Stereoelectronic model, 3
Stevastelin C3, 402–403
Stille and Stille-type transformations
description, 394
14-membered macrocyclic lactones, 395, 396
16-membered macrocyclic lactones,
395–396
Substituted tetrahydrofuran synthesis.
See Tetrahydrofuran synthesis
Sulfone lithiation approach, 216
Suzuki–Miyaura coupling, 210, 316–317
Sylvan, 147
T
Tandem Mukaiyama aldol lactonization
(TMAL) process
allylsilane addition, 6
ketene substitution, 5
reductive cyclization, 5
Tandem Suzuki coupling/macrolactonisation,
316
Tetrahydrofuran synthesis
cycloadditions
allylsilane–aldehyde, 14–18
cyclopropane–aldehyde
[3+2]-cycloadditions, 8–13
oxonium ylide approach, 18
Prins cyclization, 13–14
furan reductions, 26–27
nucleophilic additions
aryl C-glycosides, 6, 7
cyclopropyl furanones, 7
heterolytic cyclopropane ring-opening
strategy, 6
homolytic cyclopropane ring-opening
strategy, 7
keto-β-lactone cyclization, 4
lignan natural products, 3
organocatalytic aldol-Michael
reactions, 7
oxidative cyclization strategy, 8
(+)-talaumidin, 3
tandem Mukaiyama aldol
lactonization, 5
Woerpel’s model, 3
nucleophilic substitutions
(see Nucleophilic
substitutions, tetrahydrofuran)
oxabicyclic substrate
microbial oxidation, 28, 30
ring-opening metathesis, 29–34
oxidative cyclizations
cobalt catalyzed, 19
intramolecular iodoetherification, 26
manganese-mediated, 21–23
osmium-catalyzed, 23–26
palladium catalyzed, 19, 20
ruthenium catalyzed, 20–21
Prins-pinacol cascades, 27–28
stereoelectronic model, 3
zirconacyclopentadienes, 38
zirconacyclopentene approach, 37, 38
Tetrahydropyrans (THP) synthesis
C2–C3 THP-forming processes
Panek [4+2]-annulation strategies,
73–75
Petasis–Ferrier union/rearrangement,
70–73
Prins cyclization strategies (See Prins
cyclization strategies,
tetrahydropyrans)
C3–C4 THP-forming processes
retrosynthetic disconnections, 76, 77
ring-closing metathesis, 77–80
ruthenium catalysts, 76, 77
disconnections and strategies, 44
lactols/lactones, C2 functionalization
lactol reduction, 87–88
lactone reduction and reductive
acetylation, 88–91
mechanistic and structural implications,
85, 86
natural products, 44, 45
O1–C6 and C2–C3 DHP-forming
processes
Hetero-Diels–Alder (HDA) reactions,
82–85
stereochemical consequences, 81, 82
Index
439
224–225
Pd-catalyzed, 217
Wacker-type cyclization, 257
(–)-Spongidepsin, 383
Spongistatin-1, 194, 195
Steglich and Boden–Keck variants
Boden–Keck protocol, 417
description, 416
macrocyclic lactones
12-member, 417
13-member, 417, 418
14-member, 417, 418
15-member, 418, 419
16-member, 418–419
Stereoelectronic model, 3
Stevastelin C3, 402–403
Stille and Stille-type transformations
description, 394
14-membered macrocyclic lactones, 395, 396
16-membered macrocyclic lactones,
395–396
Substituted tetrahydrofuran synthesis.
See Tetrahydrofuran synthesis
Sulfone lithiation approach, 216
Suzuki–Miyaura coupling, 210, 316–317
Sylvan, 147
T
Tandem Mukaiyama aldol lactonization
(TMAL) process
allylsilane addition, 6
ketene substitution, 5
reductive cyclization, 5
Tandem Suzuki coupling/macrolactonisation,
316
Tetrahydrofuran synthesis
cycloadditions
allylsilane–aldehyde, 14–18
cyclopropane–aldehyde
[3+2]-cycloadditions, 8–13
oxonium ylide approach, 18
Prins cyclization, 13–14
furan reductions, 26–27
nucleophilic additions
aryl C-glycosides, 6, 7
cyclopropyl furanones, 7
heterolytic cyclopropane ring-opening
strategy, 6
homolytic cyclopropane ring-opening
strategy, 7
keto-β-lactone cyclization, 4
lignan natural products, 3
organocatalytic aldol-Michael
reactions, 7
oxidative cyclization strategy, 8
(+)-talaumidin, 3
tandem Mukaiyama aldol
lactonization, 5
Woerpel’s model, 3
nucleophilic substitutions
(see Nucleophilic
substitutions, tetrahydrofuran)
oxabicyclic substrate
microbial oxidation, 28, 30
ring-opening metathesis, 29–34
oxidative cyclizations
cobalt catalyzed, 19
intramolecular iodoetherification, 26
manganese-mediated, 21–23
osmium-catalyzed, 23–26
palladium catalyzed, 19, 20
ruthenium catalyzed, 20–21
Prins-pinacol cascades, 27–28
stereoelectronic model, 3
zirconacyclopentadienes, 38
zirconacyclopentene approach, 37, 38
Tetrahydropyrans (THP) synthesis
C2–C3 THP-forming processes
Panek [4+2]-annulation strategies,
73–75
Petasis–Ferrier union/rearrangement,
70–73
Prins cyclization strategies (See Prins
cyclization strategies,
tetrahydropyrans)
C3–C4 THP-forming processes
retrosynthetic disconnections, 76, 77
ring-closing metathesis, 77–80
ruthenium catalysts, 76, 77
disconnections and strategies, 44
lactols/lactones, C2 functionalization
lactol reduction, 87–88
lactone reduction and reductive
acetylation, 88–91
mechanistic and structural implications,
85, 86
natural products, 44, 45
O1–C6 and C2–C3 DHP-forming
processes
Hetero-Diels–Alder (HDA) reactions,
82–85
stereochemical consequences, 81, 82
Index
439