Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials :: Электронная библиотека попечительского совета мехмата МГУ

Главная Ex Libris Книги Журналы Статьи Серии Каталог Wanted Загрузка ХудЛит Справка Поиск по индексам Поиск Форум

Авторизация

Поиск по указателям

Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials

Обсудите книгу на научном форуме

Нашли опечатку?
Выделите ее мышкой и нажмите Ctrl+Enter

Название: Organic Synthesis: Concepts, Methods, Starting materials

Авторы: Fuhrhop J., Penzlin G.

Язык:

Рубрика: Химия/

Статус предметного указателя: Готов указатель с номерами страниц

ed2k: ed2k stats

Издание: second edition, rewise and enlarged

Год издания: 1994

Количество страниц: 432

Добавлена в каталог: 29.10.2005

Операции: Положить на полку | Скопировать ссылку для форума | Скопировать ID

Предметный указатель

Steroids      277—289
Steroids, $17\alpha$ -ethynylation      62—63 278
Steroids, $17\beta$ side-chain, construction      27 49 282—283
Steroids, $17\beta$ side-chain, oxidative degradation      118—119 283—286
Steroids, $9\alpha$ -fluorination      287
Steroids, 2- vs. 4-alkylation of 4- and 5-en-3-ones      25 156
Steroids, 21-hydroxylation      122
Steroids, conversions of natural steroids      283—289
Steroids, glycosylation of cardenolides      267
Steroids, pr. (table)      284
Steroids, redn. of the 8,9-double bond      101 104 278
Steroids, ring A, aromatization      287—288
Steroids, ring B, electrocyclic opening      289
Steroids, ring D, acid-catd. cyclization      91—92 279—280
Steroids, ring D, classic synthesis steps      49 54 55 59 82
Steroids, ring D, preformed cyclopentane units, introduction      71 73 280—281
Steroids, ring D, preformed cyclopentane units, synthesis      81 280—281
Steroids, Torgov’s synthesis      62—63 71 278
Steroids, total synthesis by acid-catalysed cyclization of a polyenynol      91—92 279—280
Steroids, total synthesis by acid-catalysed cyclization of ketone precursors      71 278—279
Steroids, total synthesis, intramol. Diels — Alder cyclizn.      280—281
Steroids, total synthesis, Robinson anellations      72—73
Stevens rearrangement      38 338
Stieglitz rearrangement      see “sec. Amines N-halo-”
Stigmasta-5,22-dien-3-ol, $(3\beta,22E)$ -, degradation of the $17\beta$ side-chain      285
Stigmasta-5,22-dien-3-ol, $(3\beta,22E)$ -, pr.      284
Stigmastan-3-ol, $(3\beta,5\alpha)$ -, remote oxidation      286
Stilbene diamine      see “Stien”
Stilbenes, synthesis by Heck coupling      43
Stille coupling, aryl tridate + organylstannane      42
Stobbe condensation      58—59
Stork reagent      328—329
Strain, steric      see “Steric strain”
Strecker’s synthesis of $\alpha$ -amino acids      50 301
Styrene      see “Benzene ethenyl-”
Succinic acid      see “Butanedioic acid”
Succinimide      see “2
Sugars      see “Monosaccharides” “Oligosaccharides”
Sugars, inexpensive derivs., pr. (table)      263—264
Sulfafurazole      307
Sulfamethoxazole      308
Sulfenic acids, esters, penam-cephem rearrangement via      315
Sulfenic acids, halides, penam-cephem rearrangement via      314
Sulfenic acids, halides, Reetz carbosulfenylation of alkenes      21
Sulfide contraction      see “Sulfur extrusion”
Sulfides, diorganyl-      see “Thioethers”
Sulfisoxazole      307
Sulfitolysis, oxidative      239—240
Sulfones, alkyl d-synthons      70
Sulfones, anions of      8 70
Sulfones, Julia — Lythgoe olefination with      34
Sulfones, reduction to thioethers      115
Sulfones, reductive desulfurization      70
Sulfones, synth. by oxn. of thioethers      80 216—217
Sulfonic acids, catalysts for cationic reactions, acetal hydrolysis      337
Sulfonic acids, catalysts for cationic reactions, acetalizations and transacetalizations      165—166 268 270 277 314 321—322
Sulfonic acids, catalysts for cationic reactions, acetalizations and transacetalizations, solid-phase ( $\mathrm{H^{+}}$ resins)      267
Sulfonic acids, catalysts for cationic reactions, acid-catalysed cyclizations      278 335—336
Sulfonic acids, catalysts for cationic reactions, aldol condensation ( $\mathrm{H^{+}}$ resin)      82
Sulfonic acids, catalysts for cationic reactions, esterifications and transesterifications      58 65 70 325 328
Sulfonic acids, catalysts for cationic reactions, esterifications and transesterifications, solid-phase ( $\mathrm{H^{+}}$ resin)      282
Sulfonic acids, esters, 1,2-cioi esters, oxiranes from      269
Sulfonic acids, esters, 1,2-cioi esters, pinacol rearr. of      32
Sulfonic acids, esters, 1-cyclopropylalkyl esters, $a^{4}$ -synthons      14—15 17 70 76
Sulfonic acids, esters, 1-decalyl esters, fragmentation      89—90
Sulfonic acids, esters, a-synthons      15—16 24 46—47 93 125 267 291
Sulfonic acids, esters, aryl esters, Stille coupling      42
Sulfonic acids, esters, oxime “esters”, Beckmann rearr.      136—137
Sulfonic acids, esters, trialkylsilyl esters, O-silylation with      321—322 325—326 328—329
Sulfonium salts, Hofmann elimn. of      38 338
Sulfonium ylides, prepn. and stability      7—8 45
Sulfonium ylides, reactions with carbonyl groups      45 79
Sulfonium ylides, reactions with electrophilic alkenes      75—76
Sulfonium ylides, reactions with imines      154
Sulfonium ylides, reactions with triorganylboranes      9
Sulfonium, dimethyl(methylthio)-, $\mathrm{[Me_{2}SSMe]CF_{3}SO_{3}}$ for activation of thioglycosides      271
Sulfonium, dimethyl-, 2-ethoxy-2-oxoethylide      8
Sulfonium, dimethyl-, methylide ( $\mathrm{Me_{2}SCH_{2}}$ ), oxiranation of carbonyl compounds      45
Sulfonium, dimethyl-, methylide ( $\mathrm{Me_{2}SCH_{2}}$ ), preparation      8 45
Sulfonium, dimethyl-, methylide, oxide      see “Sulfoxonium”
Sulfonium, diphenyl-, cyclopropylide (Trost’s reagent), syntheses with      79 335—336
Sulfonium, trimethyl-, iodide ( $\mathrm{[Me_{3}S]I}$ ), pr.      181
Sulfonium, trimethyl-, iodide ( $\mathrm{[Me_{3}S]I}$ ), ylide from      8 45
Sulfonium, trimethyl-, iodide, oxide      see “Sulfoxonium”
Sulfoxide, dimethyl-      see “Methane sulfinylbis[-”
Sulfoxide, methyl methylthiomethyl      see “Methane (methylsulfinyl)(methylthio)-”
Sulfoxides, $\beta$ -elimn. of sulfenic acids from      65 86 315
Sulfoxides, $\beta$ -oxo-      see “Ketones
Sulfoxides, anions of      8—9
Sulfoxides, chiral sulfur      8—9
Sulfoxides, Pummerer rearrangement      51 265
Sulfoxides, reduction to thioethers      115 229
Sulfoxonium, dimethyl-, methylide ( $\mathrm{Me_{2}S(O)CH_{2}}$ ), aziridination of imines      154
Sulfoxonium, dimethyl-, methylide ( $\mathrm{Me_{2}S(O)CH_{2}}$ ), cyclopropanation of 2-enones etc.      75—76
Sulfoxonium, dimethyl-, methylide ( $\mathrm{Me_{2}S(O)CH_{2}}$ ), oxiranation of carbonyl compounds      45
Sulfoxonium, dimethyl-, methylide ( $\mathrm{Me_{2}S(O)CH_{2}}$ ), preparation      8 45
Sulfoxonium, trimethyl-, iodide ( $\mathrm{[Me_{3}SO]I}$ ), pr.      181
Sulfoxonium, trimethyl-, iodide ( $\mathrm{[Me_{3}SO]I}$ ), ylide from      8 45 154
Sulfur extrusion by Stevens rearr.      38 338
Sulfur extrusion by sulfone pyrolysis      80 153
Sulfur extrusion with phosphines or trialkyl phosphites      35 38—39 59—60 261 334
Sulfur ylides      see “Sulfonium ylides”
Sulfur, (N-ethylethanalmnato)trifluoro- ( $\mathrm{Et_{2}NSF_{3}}$ , DAST), OH/F exchange      269—270 111
Sulfur, diphenylbis[2,2,2-trifluoro-1-phenyl-1-(trifluoromethyl)ethoxy]- ( $\mathrm{Ph_{2}S[OC(CF_{3})_{2}Ph]}$ , Martin’s reagent), dehydration with      282
Sulfurane      see “Sulfonium” “Sulfur”
Sulfuryl chloride isocyanate ( $\mathrm{ClSO_{2}NCO}$ , CST), cycloaddition with      153
Supramolecular chemistry      350
Swern oxidation (ClCOCOCl/DMSO)      133—134 322—323 325—327
syncat = syn-catenoid, definition      360
Synthons for N-heterocycles      147—149 152—153
Synthons, definition      1—3 4 193—196
Synthons, examples      see “Acceptor synthons” “Donos “Electrocyclizations” “Radical
Tachysterols = $\Delta^{5(10),6,8}-9,10$ -seco-sterols      34 289
Taq DNA polymerase      227
Tartaric acid, derivs., enantioselective catalysts for aldol type addition      61
Tartaric acid, derivs., enantioselective catalysts for Sharpless epoxidation      124—127 265 321 322 324—325
Tartaric acid, derivs., optical resolution with      300 301 309 327
Tartaric acid, derivs., pr.      185
Tbeoc = (2,2,2-tribromoethoxy)carbonyl, protecting group      157—158 163
TBHP      see “Hydroperoxide (1
Tce = 2,2,2-trichloroethyl, protecting group      165 216 218 220
Tceoc = (2,2,2-trichldroethoxy)carbonyl, protecting group      157—158 162—163
TCQ      see “Cyclohexadienedione tetrachloro-”
Tebbe’s methylation reagent      110 272
Template cyclizations      248 257 260 262
Terbinafine      302—303
Terminal transferase      242 243
Terpenes, cyclic      see “Steroids”
Terpenes, cyclic, hydration via boranes      130—131
Terpenes, cyclic, oxn. of allylic CH      120—121
Terpenes, cyclic, pr.      189—192
Terpenes, cyclic, syntheses, acid catd. cyclizn      90—91 93
Terpenes, cyclic, syntheses, Diels — Alder cyclization      81—82 85—86
Terpenes, cyclic, syntheses, olefination      31—33
Terpenes, cyclic, syntheses, pinacol coupling      53
Terpenes, cyclic, syntheses, Robinson anellation      71—73
Terpenes, open-chain      see “Carotenoids” “Juvenile
Terpenes, open-chain, acid-catalysed cyclization of      90—91
Terpenes, open-chain, alkylation of, via thioetbers      26
Terpenes, open-chain, homologation with acetoacetic esters      24
Terpenes, open-chain, synthesis of, Julia’s method      69—70 77
Terpenes, open-chain, synthesis of, Reformatsky reaction      44—45
Terpenes, open-chain, synthesis of, sulfur extrusion methods      39
Terramycin      317
tert-Butanol      see “2-Propanol 2-methyl-”
tert-Butyl hydroperoxide      see “Hydroperoxide 1
tert. Amines, cleavage with BrCN      309
tert. Amines, elimination of $\mathrm{R_{2}NH}$       57 73
tert. Amines, N-oxides, deoxygenation      115
tert. Amines, N-oxides, oxidants in $\mathrm{OsO_{4}}$ -catalysed oxn.      129 277

tert. Amines, oxidation to enamines or iminium ions      116 120—121 138—139
tert. Amines, synthesis by redn. of carboxamides      98 111 247 291
tert. Amines, synthesis by redn. of iminium ions      293
Tetracarbonylferrate(2-)      see “Ferrate(2-) ...”
Tetracyclines      316—318
Tetracyclo[ $3.3.1.0^{2,8}.0^{4,6}$ ]nonan-3-one      94
Tetrahedrane = $tricyclo[1.1.0.0^{2,4}]butane$       330
Tetrahydropyranyl      see “Protection”
Tetrapyrrole pigments      250—262
Tetratriacontanedioic acid      20
Tetrazole, phosphoramidite coupling catalyst      222
Thallium(1+), catalysts for displacement of tosylate      49 51
Thallium(1+), catalysts for oxn. of alkenes with $\mathrm{I_{2}/RCOOH}$       127
Thallium(3+) acetate ( $\mathrm{Tl(OAc)_{3}}$ , TTA), oxdiation of alkynes      117 132
Thallium(3+) acetate ( $\mathrm{Tl(OAc)_{3}}$ , TTA), oxidation of alkenes      117 127—128
Thallium(3+) nitrate ( $\mathrm{Tl(NO_{3})_{3}}$ , TTN) or trifluoroacetate ( $\mathrm{(CF_{3}CO_{2})_{3}Tl}$ , TTFA), ox. cleavage of 1-alkynes with      117 132
Thallium(3+) nitrate ( $\mathrm{Tl(NO_{3})_{3}}$ , TTN) or trifluoroacetate ( $\mathrm{(CF_{3}CO_{2})_{3}Tl}$ , TTFA), ox. rearr. with, of alkenes      117 129—130
Thallium(3+) nitrate ( $\mathrm{Tl(NO_{3})_{3}}$ , TTN) or trifluoroacetate ( $\mathrm{(CF_{3}CO_{2})_{3}Tl}$ , TTFA), ox. rearr. with, of ketones      118 136
Thermodynamic control, acid-catd. cyclizn      90—91 93 168 279—280
Thermodynamic control, diaslereoselective lactonization      168 327—328
Thermodynamic control, enolate formn      11—12 24—25 55 58 63 93
Thermus aquaticus DNA polymerase      227
Thexylborane      see “Borane (1
Thiiranes, reductive desulfurization, Barton olefinations      35
Thiiranes, reductive desulfurization, Eschenmoser’s sulfur extrusion      59—60 261
Thioacetals      see “1 “1 “Monothioacetals” “1
Thioesters      see “Carbothioic acids S-esters” “Sulfonothioic S-esters”
Thioethers, $\alpha$ -chlorination      314
Thioethers, $\beta$ -elimination via sulfohium salts      38 338
Thioethers, allylic, a-alkylation of anions of      26
Thioethers, allylic, rearrangements      39
Thioethers, fluorides from ( $\mathrm{NBS/Et_{2}NSF_{3}}$ )      269—270
Thioethers, oxidative cleavage      314—315
Thioethers, rearrangements      38 39 338
Thioethers, reductive desulfurization with alkali metals      39 98 113—114
Thioethers, reductive desulfurization with hydrogen/Ni-B      26
Thioethers, reductive desulfurization with Raney $nickel^{\circledR}$       76 82 98 109 113—114 156 273
Thioethers, reductive desulfurization with triphenylstannane      110—111
Thioethers, S-alkylation      38 39 338
Thioethers, S-chlorination and cleavage      314—315
Thioethers, S-oxidation to sulfones      80 216 217
Thioethers, S-oxidation to sulfoxides      315
Thioethers, S-oxidation to sulfoxides for Pummerer rearr.      265
Thioethers, sulfur extrusion from      38—39 80 338
Thioethers, synthesis by carbosulfenylation of alkenes      21
Thioethers, synthesis from diorganyl disulfides      39
Thioethers, synthesis from thiol and enoic esters      269
Thioethers, synthesis from thiol and halide      80 273 333 356
Thioethers, vinylic, hydrolysis      83
Thioethers, vinylic, synthesis by Peterson olefination      33—34
Thioethers, vinylic, synthesis by Wittig olefination      32 83
Thioethers, vinylic, synthesis via $\alpha$ -(methylsulfinyl) ketones      51
Thioglycosides, glycosylation with      271
Thioglycosides, synthesis      269
Thioketals      see “1 “1 “Monothioacetals” “1
Thiolactams, S extrusion      59—60 261
Thiols, synthesis from haloalkanes      169 269
Thionation of lactones      110—111
Thiones, olefination of      35
Thionocarbonates      see “Carbonothioates”
Thionolactones      110—111
Thionyl chloride, prepn. of acyl halides      143
Thionyl chloride, prepn. of carboxylic esters      347
Thionyl chloride, prepn. of haloalkanes from alcohols      32
Thiophenol      see “Benzenethiol”
Thiotosylate      see “Benzenesulfonothioic acid”
Thiourea, conversion of haloalkanes to thiols      169 269
Thiourea, O-O cleavage of peroxides      276—277
Thp = tetrahydropyranyl      see “Protection”
threo, definition      62 360
threo-Selectivity      see “erythro/threo”
Threonine, pr.      184
Threonine, protection      229 241
Tin organyls      see “Stannane”
Tin(2+) chloride, activation of glycosyl fluorides with $\mathrm{SnCl_{2}/Ag^{+}}$       270
Tin(2+) chloride, reduction of nitroarenes      253
Tin(4+) chloride, Lewis acid catalyst, aldol type reactions      93
Tin(4+) chloride, Lewis acid catalyst, Friedel — Crafts alkylations      233 256—257
Titanium(0), McMurry coupling      41
Titanium(2+), pincaol coupling      53
Titanium(4+), chloride tris(2-propanolate), aldol addition catalyst      62
Titanium(4+), tetrachloride, Lewis acid catalyst, aldol type reactions      56 58
Titanium(4+), tetrachloride, Lewis acid catalyst, allylstannane addn. to aldehydes      66—67
Titanium(4+), tetrachloride, Lewis acid catalyst, carbosulfenylation of alkenes (Reetz)      21
Titanium(4+), tetrachloride, Lewis acid catalyst, Michael addn. of allylsilanes (Sakurai)      90
Titanium(4+), tetrachloride, Lewis acid catalyst, opening of cyclopropanone ketals      14—15 70
Titanium(4+), tetrakis(2-propanolate), catalyst, aldol type addition      62
Titanium(4+), tetrakis(2-propanolate), catalyst, Sharpless epoxn.      124—127 265 321—326
Titanium, $\mu-chlorobis(\eta^{5}-2,4-cyclopentadien-1-yl)-(dimethylaluminum)-\mu-methylene$ - (Tebbe’s reagent), methylenation with      110 272
TMM = “trimethylenemethane” synthon      84
Tolbutamide      301
Toluene...      see “Benzene... methyl-”
Toluquinone      see “Cyclohexadienedione methyl-”
Torgov’s steroid synthesis, final steps      278
Torgov’s steroid synthesis, first step      62—63
Torgov’s steroid synthesis, second step      71
TosMIC = 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene ( $\mathrm{TsCH_{2}NC}$ )      49 51
Tosylates      see “Benzenesulfonic acid 4-methylesters”
Tosylhydrazine      see “Benzenesulfonic acid 4-methyl- hydrazide”
TPP = 5,10,15,20-tetraphenylporphine      252
Tpte protecting group      216 217
Trajectories in reactions of nucleophiles      316
trans-Selectivity      see “cis/trans”
Transcriptase, reverse      242
Transform, retro-synthetic      193—196
Triamterene      308
Triasteranone      94
Tricyclo[ $2.2.1.0^{2,6}$ ]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)- ( $\alpha$ -santalene)      42
Tricyclo[ $3.2.1.0^{2,4}$ ]oct-6-ene, $(1\alpha,2\alpha,4\alpha,5\alpha)$ -      92
Tricyclo[ $3.3.1.0^{2,8}$ ]nona-3,6-dien-9-one      94
Tricyclo[ $4.2.0.0^{2,5}$ ]octa-3,7-dienes, syn-      330 332
Tricyclo[ $4.4.0.0^{2,7}$ ]decan-3-one      3
Tricyclo[ $4.4.0.0^{2,7}$ ]decan-3-one, 6-methyl-, retro-synthesis      211—212
Tricyclo[ $4.4.0.0^{3,8}$ ]decan-4-one, 8-(acetyloxy)-, synthesis      93
Tricyclo[ $4.4.0.0^{3,8}$ ]decan-4-one, synthesis      93
Triflates      see “Methanesulfonic acid trffluoro- esters”
Trifunctional compounds, pr.      182—185 189 191 192
Trifunctional compounds, retro-synthetic analysis      202 207
Triiluoroacetyl protecting group      162 267
Trimesic acid, hydrogenation      347
Trimethylsilyl      see “Protection”
Triorganylboranes      see “Boranes”
Triprolidine      304
Triptycene = 9,10-dihydro-9,10-[1',2']benzenoanthracene, synthesis      93
Triquinacene = 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene, cyclodimerization attempts      335
Triquinacene = 2a,4a,6a,6b-tetrahydrocyclopenta[cd]pentalene, synthesis steps      141 143 165 333
Triton B      see “Benzenemethanaminium ...”
Trityl anion      see “Lithium (triphenylmethyl)-” “Potassium (triphenylmethyl)-”
Trityl cation      see “Methylium triphenyl-”
Trityl protecting group      see “Protection”
Tritylium cation      see “Methylium triphenyl-”
Troponimine, 2-amino-, “chiramt” derivative, enantioselective organocuprate addn      20—21
Trost’s reagent, diphenylsulfonium cyclopropylidc      79 335—336
Tryptamine, alkaloids from      291—293
Tryptamine, pr.      290
Tsuchihashi — Pummerer rearrangement      265
TTFA      see “Thallium(3+) trifluoroacetate”
TTN      see “2'-Deoxynucleoside 5'-triphosphates”
Twistane derivatives      93
Two-directional chain synthesis      327—328
Tyrosine, protection      229
Ullmann reaction      294—295
Umpolung, definition      1 17
Umpolung, examples      17—19
Umpolung, examples, 1-alkyne to 1-halo-1-alkyne      40
Umpolung, examples, alkene to oxirane      211
Umpolung, examples, nitroalkane to ketone      16 65—66
Undecanal, Peterson olefination of      34
Undecanoic acid, 11—halo—, alkyl coupling with      20
Undecanoic acid, 11—halo—, pr.      180

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15

О проекте