Natural Product Synthesis Using Multicomponent Reaction Strategies.pdf

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1、Chem.Rev.2009,109,4439–44864439NaturalProductSynthesisUsingMulticomponentReactionStrategies†,‡BarryB.Toure´andDennisG.Hall*DepartmentofOncologyChemistry,NovartisInstitutesforBiomedicalResearch,Inc.,250MassachusettsAvenue,Cambridge,Massachusetts02139,andDepartmentofChemistry,UniversityofAlberta

2、,Edmonton,AlbertaT6G2G2,CanadaReceivedDecember14,2008Contents5.6.PovarovThree-ComponentReaction44666.MulticomponentReactionsBasedonIsocyanides44661.Introduction44396.1.PasseriniReaction44662.TandemConjugateAddition/ElectrophilicEnolate44406.2.UgiThree-AndFour-ComponentReactions4467TrappingonR,

3、
-UnsaturatedCarbonyl7.MulticomponentReactionsInitiatedby4470Compounds[4+2]-Cycloadditions2.1.ConjugateAddition/EnolateAlkylation44407.1.Tandem[4+2]-Cycloaddition/Allylboration44702.2.ConjugateAddition/AldolCondensation44457.2.Tandemaza-[4+2]-Cycloaddition/44713.MulticomponentReactionsInitiate

4、dbya4449AllylborationNucleophilicAdditiontoCarbonylCompounds7.3.Tandemoxa-[4+2]-Cycloaddition/44713.1.AcylsilaneAddition/BrookRearrangement/4449AllylborationCarbanionAlkylation7.4.Tandem[4+2]-Cycloaddition/[2+44723.2.CyanohydrinAnionCondensation/Silyl44502]-CycloadditionTransfer/ConjugateAddit

5、ion8.MulticomponentReactionsBasedon[3+2]-and44733.3.Three-ComponentWittigReaction4451[3+3]-DipolarCycloadditions3.4.DoubleAllylationofAldehydeswithBimetallic44518.1.Three-ComponentinsituAzomethineYlide4473ReagentsFormationand[3+2]-Cycloaddition3.5.DoubleAlkenylationofSquarateFollowedby44528.2.

6、Three-ComponentinsituNitroneFormation4474AnionicOxy-CopeRearrangementand[3+3]-Cycloadditionwith3.6.Three-ComponentOxoniumFormation/44541,1-CyclopropaneDiestersAllylation9.MulticomponentReactionsCenteredonTransition44753.7.TandemMukaiyamaAldol/Knoevenagel4454MetalCatalysisCondensation/oxy-Micha

7、elAddition9.1.MultipleCross-CouplingStrategies4475(Maitland-JappReaction)9.2.DoubleAllylicAmination44773.8.GrignardReactionontoSalicylaldehydes44559.3.DoubleAllylicAlkylation4478Followedbyo-QuinoneFormationand[4+2]-Cycloaddition9.4.Othe