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

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

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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

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Предметный указатель

Diastereotopic ligands, definition      360
Diazene (diimide, diimine, $\mathrm{N_{2}H_{2}}$ ), reduction of alkenes      97 102
Diazenedicarboxylic acid, diazene from      102
Diazenedicarboxylic acid, diethyl ester, inversion-esterification with      286
Diazenedicarboxylic acid, diethyl ester, Mitsunobu reactions      160—161
Diazenes, cyclic, synthesis and $\mathrm{N_{2}}$ extrusion      35 331 334
Diazepan      307
Diazoalkanes      see “Methane diazo-”
Diazoalkanes, Barton olefination with      35
Diazoalkanes, cyclopropanation with      74—75 94
Diazotization of amino acids      202—203 312—313
DIBAH = DIBAL (diisobutylaluminum hydride)      see “Aluminum hydrobis(2-methylpropyl)-”
Diborane      see “Borane”
Dicarbonyl type compounds      see “Carboxylic acids oxo-” “Dialdehydes” “Dicarboxylic “Dioxo
Dicarboxylic acids, extended-chain, synthesis      20 37 88 328
Dicyanomethylene protecting group      166
Dicyclopropa[de,ij] naphthalene, 2a,2b,4a,4b,4c,4d-hexahydro-      332
Dieckmann condensation      55 58—59 82—83
Dieis — Alder type syntheses      81—82 84 85—86
Dieis — Alder type syntheses with hetero enes      153—154 297
Dieis — Alder type syntheses with singlet oxygen      102 276—277
Dieis — Alder type syntheses, accelerated by $\mathrm{LiClO_{4}/Et_{2}O}$       86
Dieis — Alder type syntheses, bridged bicyclic systems      78 85—86 92—93 210 212 331 333 337
Dieis — Alder type syntheses, domino Diels — Alder synthesis      337
Dieis — Alder type syntheses, fused bicyclo systems      80 81—82 84—86 318
Dieis — Alder type syntheses, intramolecular      84
Dieis — Alder type syntheses, intramolecular, in alkaloid synthesis      153—154 297
Dieis — Alder type syntheses, intramolecular, in steroid synthesis      280—281
Dieis — Alder type syntheses, pincer Diels — Alder synthesis      335—336
Dieis — Alder type syntheses, polar, with bulky reagents      86
Dieis — Alder type syntheses, reactivity and selectivity rules      85
Dieis — Alder type syntheses, retro-      see “Retro-Diels — Alder type cleavage”
Diethylpropion, $(\pm)$ -      302
Difunctional compounds, definition      2—3 50 147—149
Difunctional compounds, pr.      172—181 187—192
Difunctional compounds, rerro-synthetic analysis      199—207
Digitoxigenin      286—287
Dihydroxylation      see “1
Diimide = diimine = $\mathrm{N_{2}H_{2}}$       see “Diazene”
Diisopropylamine etc.      see “2-Propaneamine ...”
Diketones      see “Dioxo compounds”
Diketopiperazines = 2,5-piperazinediones      237
Dilution      see “High-dilution methods”
Dimethyl sulfoxide      see “Methane sulfinylbis[-”
Dimsyl anion      see “Methane sulfinylbis[- ion(1-)”
Diorganylcuprates(1-)      see “Cuprates(1-) ...”
Diosgenin, Marker degradation      283—285
Diosgenin, pr.      284
Dioxygen      see “Oxygen”
Diphenhydramine      300
Diphenoxylate      304
DIPHOS      see “Phosphine 1
Dipyrromethanes      253—255 349
Dipyrromethenes      255—257 349
Directed aldol addition      56—62
Disconnections, retro-synthetic      194
DISIAB      see “Borane bis(1
Disilazane      see “Silanamine ...”
Distamycin      343—344
Distannanes, prepn. from distannoxanes      115
Distannanes, stannylation of aryl triflatcs with      295
Disulfides, diallylic, of 2-pyridinethiol, reactive S-esters from      146
Disulfides, diallylic, of thiolactams, prepn. and S-alkylation      261
Disulfides, diallylic, S extrusion from      39
Dithioacetals      see “1 “1
Dithionite(2-), sodium, redn. of pyridinium      113
Divergent growth of dendrimers      354
DMAP      see “4-Pyridinamine N
DMP (Dess — Martin periodinane)      134 328—329
DMSO      see “Methane sulfinylbis[-”
DNA insertion (into plasmids)      243—245
DNA ligase      243—244 245—246
DNA polymerase      242 245—246
DNA synthesis, modified DNA      227 241—246 341—343 345
DNA synthesis, PCR method      226—227
Docosanedioic acid, synthesis      37
DODAC vesicles      350—351
Dodecahedrane, 1,16-dimethyl- = hexadecahydro-1,3b-dimethyl-5,2,1,6,3,4-[2,3]butanediyl-[1,4]diylidenedipentaleno[2,1,6-cde: 2',1',6'-gha]pentalene      334—337
Dodecane, 1,12-dibromo-, 1,12-diaIkylation      20
Domino — Diels — Alder reactions      209—210 337
Donor synthons      4—15
Donor synthons, $d^{0}$       1—2
Donor synthons, $d^{0}$ , ring opening with      69—70 76—79
Donor synthons, $d^{1}$       4—9
Donor synthons, $d^{1}$ , reactions of      22 45—52 65—66
Donor synthons, $d^{1}$ , stabilization of      6—9
Donor synthons, $d^{1}$ , stabilization of, by nitrogen      6 65—66
Donor synthons, $d^{1}$ , stabilization of, by phosphorus      28—32
Donor synthons, $d^{1}$ , stabilization of, by silicon      33—34
Donor synthons, $d^{1}$ , stabilization of, by sulfur      22 45 51 66
Donor synthons, $d^{2}$       9—14 18—19
Donor synthons, $d^{2}$ , stabilization of, by phosphorus      7
Donor synthons, $d^{2}$ , stabilization of, by sulfur      8
Donor synthons, $d^{3}$       14—15
Donor synthons, $d^{3}$ , stabilized by sulfur      14 26
Donor synthons, $d^{3}$ , substituted cyclopropanes      70
Donor synthons, $d^{5}$ , example      15
Donor synthons, alkyl      4—5
Donor synthons, alkyl, reactions      19—22 36—38 42—46
Donor synthons, alkyl, triorganylboranes as      9 21—22 37—38
Donor synthons, alkylidene      7—8 28—35
Donor synthons, angle of incidence to a-synthons      315—316
Donor synthons, definition      1—4
Doxycycline      317
Drugs, synthesis      299—310
Dubamine = 2-(1,3-benzodioxol-5-yl)quinoline, synthesis by Stille coupling      295
e-Synthons      see “Electrocyclic reactions”
e.e. (enantiomeric excess), definition      107 footnote
E/Z-Selectivity      see “cis/trans-Selectivity”
EC = (ethylamino)carbonyl      229 237
Elaidic acid = (E)-9-Octadecenoic acid      100
Electric eel acetylcholinesterase      277
Electrocyclic disconnection, retro-synthetic      194
Electrocyclic reactions (reactions of e-synthons)      see “Cyclization” “Ene “Ring “Ring “Rearrangements sigmatropic”
Electrocyclizations      see “Cyclizations electrocyclic”
Electron density distribution, effects on reactivity and/or regioselectivity in 1,3-dioxo 2,4-dianions      9—10 24 204
Electron density distribution, effects on reactivity and/or regioselectivity in anions of 2-en-1-ones      25
Electron density distribution, effects on reactivity and/or regioselectivity in anions of allylic thioethers      26
Electron density distribution, effects on reactivity and/or regioselectivity in anions of phosphonic diesters      29
Electron density distribution, effects on reactivity and/or regioselectivity in benzene derivs.      103—104 207—208
Electron density distribution, effects on reactivity and/or regioselectivity in dipyrromethenes      255—257
Electron density distribution, effects on reactivity and/or regioselectivity in enamines      13—14
Electron density distribution, effects on reactivity and/or regioselectivity in peroxy acids      123
Electron density distribution, effects on reactivity and/or regioselectivity in phosphonium ylides      28—29
Electronic effects, inductive      see “Hyper-conjugation”
Electronic effects, steric      see “Stereoelectronic control”
Electrophiles      see “Acceptor synthons”
Eliminations      137—142 (see also “Decarboxylation”)
Eliminations, table      138—139
Enamines, C-acylation      88
Enamines, C-alkylation      25—26
Enamines, C-nucleophilicity      13—14
Enamines, cyclopropanation      74—75
Enamines, N-acylation      153
Enamines, N-deprotonated      see “Imines N-alkyl- lithiated”
Enamines, oxidative cleavage      285
Enamines, Robinson anellation of      73 298
Enamines, synthesis by oxn. of tert. amines      138—139
Enamines, synthesis from ketones      13 88
Enantio-zeroplane, definition      359
Enantiofaces, definition      359
Enantiomeric excess (e.e.), definition      107 footnote
Enantioselective retro-synthesis      200—204
Enantioselective syntheses of $\alpha$ -ammo acids ( $\mathrm{H_{2}}$ /chiral cat.)      102—103
Enantioselective syntheses of $\alpha$ -branched aldehydes      22—23 25—26
Enantioselective syntheses of $\alpha$ -branched carboxylic acids      22—23
Enantioselective syntheses of $\alpha$ -branched ketones      25—26
Enantioselective syntheses of $\beta$ -branched ketones      20—21
Enantioselective syntheses of $\beta$ -hydroxy carboxylic acids by aldol type addition      59 61 62
Enantioselective syntheses of $\beta$ -hydroxy carboxylic acids by hydrogenation      102—103 325—326

Enantioselective syntheses of $\beta$ -hydroxy ketones      61—62
Enantioselective syntheses of 1,2-diols (chiral $\mathrm{OsO_{4}}$ -complexes)      129
Enantioselective syntheses of 2,3-epoxy alcohols      124—127 265 321—325
Enantioselective syntheses of alcohols (with chiral hydrides)      107—108
Enantioselective syntheses of homoallylic alcohols      67—69
Enantioselective syntheses of meso-diol monoesters      167—168 276—277
Enantioselective syntheses of steroids      278—279 280 282
Enantiotopic group selectivity      126 167—168 276—277 359
Enantiotopic ligands, definition      359
endo-Peroxide of cyclic dienes      102 276—277
endo/exo-Selective reactions, acid-catd. aldol type cyclizn.      93
endo/exo-Selective reactions, alkylation with $\mathrm{R_{2}CuLi}$       20
endo/exo-Selective reactions, epoxidation and glycolization      123 209—210
endo/exo-Selective reactions, [2+4]cycloadditions      78 85—86 92 209—210 297
Endonucleases, restriction-      243
Endoperoxides from 1,3-dienes      102 276—277
Ene reactions (cycloadditions with H transfer), addition of propynoic esters      282—283
Ene reactions (cycloadditions with H transfer), intramolecular, in alkaloid synth.      297—298
Ene reactions (cycloadditions with H transfer), oxidation with $\mathrm{SeO_{2}}$       119 122
Ene reactions (cycloadditions with H transfer), rearrangement of thioethers with benzyne      39
Enol esters, oxidative cleavage      280
Enol esters, preparation      58 280
Enol ethers, addition of nitrosyl chloride      268
Enol ethers, cyclopropanation      74—75 83
Enol ethers, hydrolysis      49 103—104 278
Enol ethers, iodoetherification      272
Enol ethers, oxidative cleavage      285
Enol ethers, preparation by alcohol addn. to alkynes      64
Enol ethers, preparation by Birch reduction of alkoxyarenes      87 97 103—104 278
Enol ethers, preparation by HX-elimination of a-halo ethers      268
Enol ethers, preparation by olefination with $\mathrm{Ph_{3}P=CHOR}$       48—49
Enol ethers, preparation by Tebbe-olefination of esters      110 272
Enolate type anions, nucleophilicity differences      24—25 56
Enolate type anions, oxidation of      121—122
Enolate type anions, preparation from $\alpha,\beta$ -unsatd. ketones, with lithium      73
Enolate type anions, preparation from carbonyl type compounds      9—13 22—23 26 57—58 60—63
Enolate type anions, preparation from carbonyl type compounds, E/Z-selective      12—13 22—23 26 60—62
Enolate type anions, preparation from enol esters and enol silyl ethers      24 57—58 73 281
Enolate type anions, preparation with organylcopper reagents      277
Enolate type anions, preparation with organylmagnesium reagents      281
Enolate type anions, reactions of      22—27 55—65 71—74
Enolate type anions, silylated, oxidative coupling with $\mathrm{Ag^{+}}$       65
Enolate type anions, trapping with $\mathrm{CF_{3}SO_{3}BR_{2}}$       12—13 61—62
Enolate type anions, trapping with $\mathrm{CF_{3}SO_{3}SiBu^{t}Me_{2}}$       325
Enolate type anions, trapping with 1-propen-2-ol acetate      58
Enolate type anions, trapping with chlorotrimethylsilane      11 58 73 75 83 281
Enzymatic reactions      167 276—277
Enzyme-cleft models from Kemp’s acid      347
Ephedrine, N-methyl-, (R,R)-, chiral hydride from      107—108
Ephedrine, N-[2-(dimethylamino)ethyI]-(-)-, chiral cuprate reagents from      20—21
Ephedrine, stereoisomers, pr.      290
Ephedrine, stereoisomers, synthesis      302
Epimerization      see “Racemization”
Epimerization at enolizable carbon atoms      32 78 93 265 277 283 322—323
Epimerization at enolizable carbon atoms, prevention      277 299
Epimerization of hydroxy groups by inversion-esterification      160—161 286
Epimerization of hydroxy groups via keto groups      288—323
Epimerization of tetracyclines      317
Episullldes      see “Thiiranes”
Epoxides      see “Oxiranes”
Equilibrium control      see “Thermodynamic control”
Ergocalciferol (vitamin $\mathrm{D_{2}}$ )      289
Ergosta-5,7,22-trien-3-ol, $(3\beta,22E)$ - (ergosterol), pr.      284
Ergosta-5,7,22-trien-3-ol, $(3\beta,22E)$ - (ergosterol), ring opening      289
Ergotamine, synthesis steps      143
Erythrcmolide A seco acid, total synth.      32D—323
Erythrinane (= indolo[7a,1-a]isoquinoline) alkaloids by amine-phenol coupling      294
erythro, definition      62 360
erythro/threo-Selective syntheses      see “Asymmetric induction”
erythro/threo-Selective syntheses, $\alpha$ -alkylation of 3-hydroxy esters      27 325—326
erythro/threo-Selective syntheses, addn. of anions to oxiranes      63—64 204
erythro/threo-Selective syntheses, aldol type additions      60—62 322—323
erythro/threo-Selective syntheses, alkylation of sulfoxides      8—9
erythro/threo-Selective syntheses, allylation of carbonyl groups      66—67 325—326
erythro/threo-Selective syntheses, carbosulfenylation of alkenes      21
erythro/threo-Selective syntheses, dihydroxylation of alkenes      129
erythro/threo-Selective syntheses, epimerization via enolates      265
erythro/threo-Selective syntheses, reduction of ketones      106—107 322—323
erythro/threo-Selective syntheses, Sharpless epoxidation of allylic alcohois      125—127 265 322 324—325
Erythromycins      319
Erythronolides A and B, total synth      319—320
Eschenmoser’s principle      34—35 261
Eschenmoser’s sulfur extrusion      59—60 261
Ester condensations      55 58—59 81—83
Ester pyrolysis      see “ $\beta$ -Eliminations”
EsterilTcation      see “Carboxylic acids esters”
Esters      see “Carboxylic acids esters” “Sulfonic esters”
Estr-4-ene-3,17-dione, (+)-, total synth.      279
Estra-1,3,5(10)-trien-17-one, $(\pm)$ -, synthesis      281
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- (estrone), $17\alpha$ -ethynylation      62—63
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- (estrone), synthesis by aromatization of ring A      287—288
Estra-1,3,5(10)-triene-3,17-diol, (+)- (estradiol), total synthesis      280
Estra-1,3,5(10)-triene-3,17-diol, 17-acetate, partial synthesis      287
Estradiol, ethynyl- = 19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol, $(17\alpha)$ -      62—63
Ethanal      see “Acetaldehyde”
Ethanamines, N,N-dialkyl-2-halo-, drugs from      303—304
Ethanamines, N,N-dialkyl-2-halo-, pr.      180
Ethane, nitro-, $d^{1}$ -synthon      6 301 302
Ethaneamine, N,N-diethyl- ( $\mathrm{Et_{3}N}$ ), $\alpha$ -deprotonation of ketones      11 71
Ethaneamine, N,N-diethyl- ( $\mathrm{Et_{3}N}$ ), elimn. of HCl from $\mathrm{Cl_{2}CHCOCl}$       83 276
Ethaneamine, N-ethyl, Li salt ( $\mathrm{LiNEt_{2}}$ ), conversion of epoxides to allylic alcohols      27
Ethanedioyl dichloride (oxalyl chloride), preparation of acid halides with      143
Ethanedioyl dichloride (oxalyl chloride), Swern oxidation with ClCOCOCl/DMSO      133—134 322—323 325—327
Ethaneperoxoic (peroxyacetic) acid, Baeyer — Villiger oxn. with      136 276 319—320
Ethaneperoxoic (peroxyacetic) acid, epoxidation with      34 88 123
Ethaneperoxoic (peroxyacetic) acid, trifluoro-, Baeyer — Villiger oxidation with      282
Ethaneperoxoic (peroxyacetic) acid, trifluoro-, relative reactivity      123
Ethanoic acid      see “Acetic acid”
Ethanol, 2,2,2-trichloro-, phosphate protection      167 216—218 220
Ethanol, 2,2,2-trichloro-, pr.      179
Ethanol, 2-(diethylamino)- and 2-(dimethylamino), drug syntheses with      300
Ethanol, 2-(diethylamino)- and 2-(dimethylamino), pr.      177
Ethanol, 2-cyano- = 3-hydroxypropanenitrile, phosphate protection, 2-cyanoethyl ester (Ce)      166—167 216 218 220—224
Ethanol, 2-cyano- = 3-hydroxypropanenitrile, pr.      176
Ethanol, 2-[[4-(triphenylmethyl)phenyl]thio]- (TpteOH), phosphate protection      216—217
Ethanol, ion(1-) (ethanolate, ethoxide), enolization with      10 23 72—73 283
Ethanone, 1-cyclopropyi-, pr.      189
Ethanone, 1-cyclopropyi-, synthesis      130
Ethanone, 2-hydroxy-1,2-diphenyl- (benzoin), cyclic carbonate, N-prntecting reagent      164
Ethene, bromo- (vinyl bromide), cyclopropanation of      74
Ethene, bromo- (vinyl bromide), Grignard reagent from      63
Ethene, bromo- (vinyl bromide), pr.      179
Ethene, chloro-, lithiation      5
Ethene, methoxy-, cyclopropanation of      74—75
Ethene, methoxy-, pr.      174
Ethenone (ketene), $d^{2}$ -synthon      58—59
Ethenone (ketene), acetylation with      58—59 75
Ethenone (ketene), cyclopropanation of      75
Ethenone (ketene), dichloro-      83 276
Ethenone (ketene), dichloro-, [2+2]cycloaddn. with      83 276
Ethenone (ketene), pr.      174
Ethers      see “Protection”
Ethers, $\beta$ -iodo-, reductive $\beta$ -elimination      326—327
Ethers, $\beta$ -iodo-, synthesis from alkenes      272 326
Ethers, oxidation to esters or lactones      118 134—135
Ethers, synth. from esters or lactones      110—111 272
Ethoheptazine, $(\pm)$ -      304
Ethyne, 17-ethynylation of steroids      62—63 278
Ethyne, addn. to carbonyl groups      52
Ethyne, ethoxy-, lithiated, carboxymethyl $d^{2}$ -synthon      64—65 325 327—328
Etioporphyrin      256
Exhaustive dehydrogenation      139—140 338
Expansion of rings      see “Ring expansion”
Extrusion of carbon dioxide      80
Extrusion of carbon monoxide      78 330
Extrusion of molecular nitrogen      35 331 334
Extrusion of sulfur      35 38—39 59—60 80 261 334 338
Extrusion of sulfur dioxide      80
Favorskii rearrangement      78 84 211
Ferrate(2-), tetracarbonyl-, acyl d-synthons from      17 46—47

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