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IntroductiontoOrganicSynthesis有机合成初步6/11/20211
合成化学家在旧的自然界旁又建起了一个新的自然界R.B.WoodwardE.J.CoreyRetro-syntheticanalysis逆合成分析TheNoblePrizein199020世纪《TheLogicofChemicalSynthesis》6/11/20212
1.Retrosyntheticanalysis(逆合成分析)Inthisprocedurethetargetmoleculeistransformedprogressivelyintosimplerstructuresbydisconnectingselectedcarbon-carbonbonds.Thesedisconnectionsrestontransforms,whicharethereverseofplausiblesyntheticconstructions.Eachsimplerstructure,sogenerated,becomesthestartingpointforfurtherdisconnections,leadingtoabranchedsetofinterrelatedintermediates.Aretrosynthetictransformisdepictedbythe=>symbol,asshowninnextslide.Onceacompleteanalysishasbeenconducted,thedesiredsynthesismaybecarriedoutbyapplicationofthereactionsunderlyingthetransforms.6/11/20213
SynthonEquivalentDisconnectionrestontransforms6/11/20214
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SynthonEquivalentPolarInversion极性反转6/11/20216
PolarInversion6/11/20217
Symbol6/11/20218
FunctionalGrouptransforms6/11/20219
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2.DisconnectiononTMswithoutFG——addingFGTM：targetedmolecule目标分子6/11/202111
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3.DisconnectiononTMswithmonoFGApplicationofMalonicester6/11/202114
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80%99%80%6/11/202117
酮式烯醇式ApplicationofEthylAcetoacetatepKa＝116/11/202118
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ApplicationofEpoxy（环氧）compounds6/11/202122
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DisconnectiononCyclohexene6/11/202125
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Birch还原6/11/202127
4.DisconnectiononBifunctionalgroups（1）,-unsaturatedcompounds6/11/202128
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（2）,-unsaturatedcarboxylicacid6/11/202130
（3）-Hydroxyester6/11/202131
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（4）1,3-bicarbonyl6/11/202133
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（5）1,4-bicarbonyl6/11/202135
（6）1,5-bicarbonyl——迈克尔（Michael）加成反应6/11/202136
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（7）1,6-bicarbonyl6/11/202140
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Birch还原6/11/202142
4.Rearrangment6/11/202143
嚬哪醇重排：6/11/202144
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5.Examples6/11/202146
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AsynthesisofN-ethyl-2-aminomethylspiro[3.3]heptanefromstartingcompoundshavingnomorethanthreecontiguouscarbonatomsisrequired.6/11/202156
Asynthesisof2-acetyl-2-methylbicyclo[2.2.2]octanefromcyclohexeneandotherstartingcompoundshavingnomorethanfourcontiguouscarbonatomsisrequired.6/11/202157
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Asynthesisof2,7-dimethyl-4-octanonefromstartingcompoundshavingnomorethanfourcontiguouscarbonatomsisrequired.6/11/202160
Asynthesisof1,4,6--trimethylnaphthalenefrompara-xyleneandotherstartingcompoundshavingnomorethanfourcontiguouscarbonatomsisrequired.6/11/202161
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BiomimeticSynthesis仿生合成21世纪6/11/202163
托品酮（Tropinone）的仿生合成6/11/202164
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