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1、REVIEWSTheDiels±AlderReactioninTotalSynthesisK.C.Nicolaou,*ScottA.Snyder,TamsynMontagnon,andGeorgiosVassilikogiannakisTheDiels±Alderreactionhasbothfacilitatingcomplexmoleculecon-reviewinthecontextoftotalsynthesisenabledandshapedtheartandsciencestruction,theDiels±Aldercycl
2、oaddi-toillustrateitsoverallversatilityandoftotalsynthesisoverthelastfewtionhasaffordednumerousandun-underscoreitsvastpotentialwhichhasdecadestoanextentwhich,arguably,paralleledsolutionstoadiverserangeyettobefullyrealized.hasyettobeeclipsedbyanyotherofsyntheticpuzzlesprov
3、idedbynaturetransformationinthecurrentsyntheticintheformofnaturalproducts.InKeywords:biomimeticsynthesis¥repertoire.Withmyriadapplicationsofcelebrationofthe100thanniversaryofcycloaddition¥Diels±Alderthismagnificentpericyclicreaction,Alder×sbirth,selectedexamplesofthereact
4、ion¥moleculardiversity¥totaloftenasacrucialelementinelegantawesomepowerofthereactionhesynthesisandprogrammedcascadesequenceshelpedtodiscoverarediscussedinthis1.IntroductionAfternumerousnear-discoveriesofthe[42]cycloadditionreactionbyseveralluminariesinthefieldoforganicche
5、mistryduringtheearlypartofthe20thcentury,[1,2]thekeeninsightofProfessorOttoDiels[3]andhisstudent,KurtAlder,[4]inproperlyidentifyingtheproducts(4and6,Scheme1)arisingfromthereactionofcyclopentadiene(1)withquinone(2)denotesahistoriceventinthefieldofchemistryforwhichthesetwoi
6、ndividualswererewardedwithareactionthatwouldhenceforthbeartheirnames.[5]Withpropheticfore-sight,DielsandAlderclearlyanticipatedtheimportanceofthisdiscoveryintheirlandmark1928paper,particularlyasappliedtonaturalproductsynthesis,throughthefollowingremark:™Thusitappearstoust
7、hatthepossibilityofsynthesisofcomplexcompoundsrelatedtooridenticalwithnaturalproductssuchasterpenes,sesquiterpenes,perhapsevenalkaloids,hasbeenmovedtothenearprospect.∫However,inanintriguingmomentofscientificterritoriality,whichmightappearslightlyoff-colororevenamusingtoac
8、ontem-[*]Prof.Dr.K.C.Nicolaou,S.A.Snyder,Dr.T.Montagnon,Dr.G.VassilikogiannakisScheme1.Thediscov