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基于分子内Diels-Alder反应的活性天然产物全合成.docx

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基于分子内Diels-Alder反应的活性天然产物全合成 Title:TotalSynthesisofNaturalProductsviaIntramolecularDiels-AlderReaction Introduction: Totalsynthesisofnaturalproductshasbeenafruitfulareaofresearchinorganicchemistry,enablingtheidentificationoftheirstructures,determinationoftheirbiologicalactivities,andthedevelopmentofsyntheticmethodologies.TheDiels-Alderreaction,discoveredbyOttoDielsandKurtAlderin1928,isanimportantandversatiletoolinorganicsynthesis.TheintramolecularDiels-Alderreaction,whereboththedieneanddienophilearepartofthesamemolecule,hasproventobeapowerfulstrategyforthesynthesisofcomplexnaturalproducts.ThispaperaimstohighlightsomenotableexamplesofthetotalsynthesisofnaturalproductsusingintramolecularDiels-Alderreactions. 1.KeyconceptsoftheDiels-AlderReaction: TheDiels-Alderreactionisapericyclicreactionthatinvolvestheformationoftwonewσbondsandaπbond.Itisinitiatedbytheinteractionbetweenaconjugateddieneandadienophile,withtheformationofacyclohexenering.Thereactionishighlystereoselective,withthedieneanddienophileaddinginasynfashion.ThereactioncanbeacceleratedbyboththermalandLewisacidcatalysis. 2.ApplicationsoftheintramolecularDiels-Alderreactioninnaturalproductsynthesis: 2.1.Tetracyclineantibiotics: Tetracyclinesareagroupofantibioticswithabroadspectrumofactivityagainstbothgram-positiveandgram-negativebacteria.WoodwardandDoeringpioneeredthesynthesisoftetracyclinein1958usinganintramolecularDiels-Alderreaction.Thislandmarksynthesiscontributedtotheunderstandingofthestructureandstereochemistryoftetracycline. 2.2.Cembranoidditerpenes: Cembranoidditerpenesareaclassofnaturalproductsfoundinmarineorganismsthatexhibitawiderangeofbiologicalactivities.In2009,Baranandcoworkersachievedthetotalsynthesisoftelopathone,acembranoidditerpene,usinganintramolecularDiels-Alderreactionfortheconstructionofthepolycyclicframework.Thesynthesisprovidedaccesstosufficientmaterialforbiologicalevaluationandconfirmedtheproposedstructure. 2.3.Strychnine: StrychnineisacomplexalkaloidthatoccursnaturallyintheseedsoftheStryc