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Reduction Disconection

Reduction Disconection

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Published by Gabriel Flores

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Published by: Gabriel Flores on Mar 22, 2012
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References to tables are given in bold type.acetals 2–3symmetrical cyclic 209–210acetylenes
alkynesAchilles Heel strategy 63–64acids, halogenation 47acyl anion equivalents 167–170,187–189acylationby ketene dimers 254Friedel-Crafts 8–9, 209acyloin reaction 180–182adipic acid 199adrenaline 50AIDS drugs 119–120alcoholsC-C disconnections 69–76dehydration to alkenes 107derivatives 27–28oxidation 72protecting groups for 65–66symmetrical 78–80synthesis 70–71, 74–751,2 C-C disconnections 73–74examples 74–75aldehydesfrom alcohols 72synthesis by acylation 93–96aldol reaction 134, 321–322alkaloids 275alkenescyclisation by carbene insertion 231–234from alkynes by reduction 116–117hydrationsynthesisof 1,2-difunctionalised compounds 170–171by elimination 107–108by Wittig reaction 108–112alkylation reactionsamination 56–57aromatic compounds 9–10, 10–11alkynesin anti-AIDS drug 119–120reduction to alkenes 116–117
Organic Synthesis: The Disconnection Approach. Second Edition
Stuart Warren and Paul Wyatt
2008 John Wiley & Sons, Ltd
allylic carbons 177–179amides, as protecting groups 62–64aminesoverview 53–54primary 55, 56–57secondary 55, 57tertiary 56from nitro compounds by reduction 161–162monomorine I synthesis 57–59reductive amination 55–56amino acids 31–32Aphox 306Arndt-Eistert procedure 237–238aromatic compoundsacylation 8–9disconnection 7–8functional group addition, general strategy17–22functional groups, and reactivity 18reduction 273–277aspartame 64axial attack 89–90azides 56Baeyer-Villiger reaction 203–204, 253Beckmann rearrangement 253benzene rings, Birch reduction 274–275benzocaine 7–8benzoin condensation 174–175biotin 177–179Birch reduction 274–275aromatic carboxylic acids 276–277brevianamide 194bromohexanoic acid 47
-butyloxycarbonyl group 64carbenesmetal complexes 233synthesis by
-elimination 232–233carbobenzyloxy (Cbz) groups 63carbon acids 131–132carbon nucleophiles 70
carbonyl compounds1,2 di- 173–1741,3 di- 136–1371,4 di- 190–1911,5 di- 151–1591,6 di- 199–204and amination 54
-hydroxy 133–135by conjugate addition 98–100cyclisation to five-membered rings 255–256derivatives 23–25dicarbonyl 129–132intramolecular reactions 140–141nucleophilicity 129
-unsaturated 135–136
-functionalisation 172–173carbonyl condensations, compounds whichcannot enolise 141–144carboxylic acidsC-C disconnection 72–73reduction 276–277Cbz group 63chemoselectivity 29–34chirality
stereochemistrychloroacetyl chloride 47
-chrysanthemic acid 230citronellal 196–197Claisen rearrangement 265–267clopirac 302–303columbiasin A 271–272conformational control 89–90conjugate addition 36, 37–38, 321–322of acyl anion equivalents 187–189carbon nucleophiles 104–106nitro-alkanes 163convergence 314–318, 319copaene 293–295Cope rearrangement 265coriolin 292, 292–293cyanide ion 169–170, 187cyclisation 48–49, 217–219three-membered rings 219cyclopropanes 229–231sulfonium ylids 234–235four-membered rings 220–221, 245, 280–282by ionic reactions 248five-membered rings 221–223, 255–258six-membered rings 223–224, 270–271Diels-Alder reaction 201–202seven-membered rings 224–226disconnections for small rings 280–282general considerations 217–219ketenes 251–254kinetic and thermodynamic factors
ring expansion and contraction 238–240Robinson annelation 156–157salbutamol 50–51and selectivity control 279–280cyclomethycaine 30–31cyclopentanes 257–258by conjugate addition 258cyclopropanes 229–231damascenone 262darifenacin 75dendrimers 267diarylketones 182–183diastereoisomers 83–85diazoalkanes 237–238, 238–240dicarbonyl compounds 193–196dichlorocarbene 232dicyclomine 273–274Diels-Alder reaction 121–127, 269, 271–273,320–3211,6-dicarbonyl compounds 201–202functional group interconversion (FGI) of products 126molecules with several chiral centres 291nitroalkene synthesis 164–165regioselectivity 124–125in water 126–127dienesstereospecificity 122–123synthesis 117by Wittig reaction 112dienoestrol 180difunctionalised compounds1,1-difunctionalised 41–431,2-difunctionalised 39–411,3-difunctionalised 37, 38
see also
disconnections, two-groupdihydropyran 63dimedone 230disconnections1,5-difunctionalised compounds 151–158overview 1–2, 80symbol 7example 2–4guidelines 80order of events 17–18C-Cone-group1, 1 70–731, 2 73–75other 75–76simplification 77–78starting materials 78–79symmetry 78two-group1,2-difunctionalised compounds 167–1761,3-difunctionalised compounds 133–1381,4-difunctionalised compounds 185–1921,5-difunctionalised compounds 151–1591,6-difunctionalised compounds 199–205Diels-Alder reactions 129–132C-heteroatom 301–303polarity reversal 45–46
carbonyl compounds 207–214heterocyclic compounds 301–304two functional groupsas analytic preliminary 43–44overview 35–36recognition 36
see also
Diels-Alder reactions;disconnections, C-C, two-groupdisparlure 111DMF 94–97electrocyclic reactions 261–263elm bark beetle 2enamines 147–148enantiomers 83–85enolates1,3-dicarbonyl compounds 97–98alkylation to cyclopropanes 229–231anionic 131–132,
lithium 96–97, 145–146enolsalkylation 96–98specific 144–148enones, spiro 210–211epoxides 45–46rearrangement reactions 241equilibrium reactions 148–149esterslithium enolates 145–146synthesis by acylation 93–96ethersas protecting groups 62synthesis 25–26Favorskii rearrangement 242–243fencamfamin 164fentiazac 303–304fluconazole 40fluoxetine 12–13folded molecules 90stereochemistry 292–293formaldehyde, Mannich reaction 143–144Friedel-Crafts reactions 8–9, 209functional group addition (FGA)1,4-difunctionalised compounds 196–197aromatic compounds 10–11carbonyl compounds 191order of events 17–18functional group interconversion (FGI) 7–8Diels-Alder products 126functional groupschoice and yields 33functionalisation, allylic and benzylic177–179interaction 17–18and reactivity 18two-group disconnections 35–36
see also
protecting groupsfurans, electrophilic substitution309–310furfural 119gingerol-6 146grandisol 168guanacastetepenes 272–273halicholactone 235halogenationacids 47ketones 46–47Henry reaction 163heterocyclic compounds1,5-dicarbonyl compounds 158aromatic 301–311indoles 307saturated 217–227substitution reactions 308–311homoenolates 189–1904-hydroxyketones 187indoles, electrophilic substitution 309–310indomethacin 307–308intramolecular reactions, cyclisations217–226 jasmone 116–117 juvabione 295–298ketenes 251–254ketonesalkylation, regiospecific 101–103cyclopentyl 256–257from alcohols 71–72halogenation 46–47synthesis 95by acetylene hydration 118by acylation at carbon 93–96by alkylation of enolates 96–98by conjugate addition 98–100by oxidation of alcohols 72unsaturated 133–149Knoevenagel reaction 144lactones 148–149, 208–209laulimalide 65LHASA program 2lithium enolates 96–97, 145–146
-lycorane, stereochemistry 323–324Mannich reaction 143–144maritidine 275metal carbenoids 233–234metaproterenol 172methoxatin 315–318methylenomycin 186–187

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