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1、Chem.Rev.1991,91,1237-12861237RadicalReactionsinNaturalProductSynthesisCRAIGP.JASPERSE'DepartmentofChemktry,UnlversityofNorthDakota.Box7185,UniversityStatbn,GmnlForks,NorthDakota58202DENNISP.CURRAN'Wa"tofChemistry.UniversityofPittsburgh,Pittsburgh,Pennsylvani
2、a15260THOMASL.FEVIG'ScherfngPkuBhCorpOnrlJon,W25,60OrangeStreet,Bhmfkhl,NewJersey07003ReceivedFebruary8,1991(RevisedManuscriptReceivedMy20,1991)ContentsVIII.ConcludingRemarks1281Acknowledgments1281ReferencesandNotes1282I.Introduction1237I.Introduction11.TheTi
3、nHydrideMethod1239A.Introduction1239Theuseofradicals'inorganicsynthesishasincreased8.CarbacycleFormationwithTinHydride1239dramaticallywithinthelastdecade.Atthebeginning1.Introduction1239ofthe1980's,theplaceofradicalreactionsinnatural2.5-MemberedRings1240produ
4、ctstotalsynthesiswaslimitedtoafewimportant3.0-MemberedRings1245functionalgrouptransformations(suchastheBarton-4.LargeRings1247McCombiereaction2).However,duringthepastdec-C.CarbacycleRingOpeningwithTinHydride1247ade,radicalcarbon-carbonbond-formingreactionshav
5、eD.OxacycleFormationwithTinHydride1248growninimportancetothepointwheretheyarenowE.NitracycleFormationwithTinHydride1251routinelyconsideredinstrategylevelplanningofcom-F.IntermolecularRadicalAdditionswithTin1252plextargets?RecentprogressinradicalchemistryhasHy
6、dride(GieseReactions)beenthoroughlyreviewedfromthestandpointof111.TheMercuricHydrideMethod1255structure,reactivity,andsyntheticmethod^.^-^TheIV.TheFragmentationMethod1256subjectofthepresentreviewistheuseofradicalre-A.IntermolecularReactionswiththe1250actionsi
7、nnaturalproductsynthesis.BysummarizingFragmentationMethodaccomplishmentsofthelastdecade,wehopetofurtherB.IntramolecularCyclizationswiththe1257exposetheuniquefeaturesofradicalreactionsforFragmentationMethodsyntheticapplicationsandtoencouragethedevelop-V.TheAto
8、mIGroupTransferMethod1259mentofnew,moresophisticatedapplications.A.Introduction1259Thereviewwillemphasizeissuesofreactivity,che-8.HydrogenTransfer1260moselectivity,regioselectivity,andste
