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1、Welcome!OnthisCDyouwillfindacopyofalltheschemesinClassicsinTotalSynthesisIIamalgamatedbychapterintotwenty-twopdffiles.Wehaveprovidedtheseschemesforeducatorstocreateoverheadsorelectronicpresentationsofthistextbook,forstudentstotakenotesduringlectures,orforanyotherusethatwillassist
2、inreadingourbook.Enjoy!K.C.NicolaouScottA.SnyderINTRODUCTIONMeMeOMeOHOOOMeOMeMeOMeMeOOOOOOOClOOOOOOOOOOMeOOHOMeMeHOOHOHOOHOHOHClNO21:everninomicin13,384-1OMeMeMeOMeHCO2HHOHOOHNONHOMeOMeNMeOHOMeHNOHAcOSHOHHOOHOMeHHOHNMe4:dynemicinANNOHNHOHOHOHMe3:ecteinascidin743NMeO2:manzamineAMe
3、HOHHNNHOHMeMeOOMeMeO2CMeO2COHOHMeOOAcOOOHNHOHMeONMe5:resiniferatoxinCOMeMe2MeO6:vinblastineMeOMeOCO2OHMeOHONHNMeMeNH7:isochrysohermidinHMeMeOMeMeHHNHNHNMeNH8:colombiasinANHNNNNHMeHHNOMeMeHNHNNNNHH9:psycholeineMeMe11:quadrigemineCOHHNOOHO10:quinineHOOOHMeOOOMeOOOOOOMeMeCO2H12:CP-2
4、25,917CO2H13:CP-263,114Figure1.Selectedstructuresofcomplexnaturalproducts.OHOMeNOMeMeHOOHHOMeHNMeOOMe2MeOHOOHOOOHONOOHMeOHOMeMeO15:aspidophytine14:bisorbicillinolClOOHOClOHOOOHHHHNNNNNNMeROHHOOHOMeNHSONH2MeHONHO2COHOOHHOOOHO16:vancomycin17:R=H,epothiloneA18:R=Me,epothiloneBMeONOH
5、MeOHMeMeHOMeNOHOHONMeHOOMeOMeHOHOOHMeNMe19:longithoroneAHMeMeMeO20:okaramineNMeOMeOHOOHOOOOOHOMeOMeMeMeOHMeOMeMeMeMeMeHOOHOHMeHOOHOOMeOMe22:trichodimerolOMeMe21:swinholideAMeMeMeHHMeOHMeNHNOMeNHONMeOHNClHOOOHOHOOOClHOHHONHONHNHMeOOHMeOH23:FR18287724:plicamine25:diazonamideAFigure
6、1.Continued.HOOHOORROOCSA(6equiv),HHOOCH2Cl2,-94°C,3hOOOHHO(44%)BidirectionalHHtetracyclizationOHOHHOHO2627MsCl,py,4-DMAP,(50%at60%0°C,1h;25°C,1hconversion)HHHOOMsRROOO0.1OOMNaOAc,HHHHHOAc,OO40°C,12hOO(65%)HHHHOHOHOHOH29:glabrescrol28Scheme1.Anelegant"biomimetic"cyclizationsequen
7、ceaspartofCoreyandXiong'sexpedienttotalsynthesisofglabrescol(29).OOMeMeMei-PrOOi-PrLiMei-PrOOO4π-ElectronOO31conrotatoryOOi-PrOOringLiOi-PrOOopeningtransAdditioni-PrOO30MeMe323331,cisAddition8π-ElectronconrotatoryLiringclosingMeMeMeMeMeMeOHOHOi-PrOOi-PrOORingi-PrODianionicOoxy-Co
8、peOopeningOi-PrOi-PrOi-PrOOOOO353436Aldo
