Metathesis Reactions in Total Synthesis.pdf

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1、ReviewsK.C.Nicolaouetal.SynthethicMethodsMetathesisReactionsinTotalSynthesisK.C.Nicolaou,*PaulG.Bulger,andDavidSarlahKeywords:DedicatedtoProfessorThomasJ.Katzalkenemetathesis·alkynemetathesis·ontheoccasionofhis70thbirthdayenynemetathesis·naturalproducts·totalsynthesisAngewandteChemie44902005Wi

2、ley-VCHVerlagGmbH&Co.KGaA,WeinheimDOI:10.1002/anie.200500369Angew.Chem.Int.Ed.2005,44,4490–4527AngewandteMetathesisReactionsChemieWiththeexceptionofpalladium-catalyzedcross-couplings,noFromtheContentsothergroupofreactionshashadsuchaprofoundimpactonthe1.Introduction4491formationofcarbon–carbonbo

3、ndsandtheartoftotalsynthesisinthelastquarterofacenturythanthemetathesisreactionsofolefins,2.TheAlkene-MetathesisReaction4493enynes,andalkynes.Herein,wehighlightanumberofselectedexamplesoftotalsynthesesinwhichsuchprocessesplayedacrucial3.TheEnyne-MetathesisReaction4512roleandwhichimpartedtothese

4、endeavorscertainelementsof4.TheAlkyne-MetathesisReaction4517novelty,elegance,andefficiency.Judgingfromtheirshortbutimpressivehistory,theinfluenceofthesereactionsinchemical5.SummaryandOutlook4520synthesisisdestinedtoincrease.1.IntroductionEversincethebirthoftheartoforganicsynthesis,asmarkedbyWöh

5、lerssynthesisofureain1828,progressinthisfieldhas,toalargedegree,beendependentonourabilitytoconstructcarbonframeworksthroughcarbon–carbonbond-[1][2]formingreactions.TheGrignard,Diels–Alder,andWittig[3]reactionsarethreeofthemostprominentsuchprocessesthatplayeddecisiverolesinshapingthescienceofch

6、emicalsynthesisasweknowittoday.Duringthelastquarterofthepreviouscentury,twomoresuchreactionsemergedasrivalstotheaforementionedcarbon–carbonbond-formingproc-esses:thepalladium-catalyzedcross-couplingreactionsandthosecollectivelyknownasmetathesisreactions.AsamostScheme1.Themostcommonlyemployedalk

7、ene-metathesisreactionsstringenttest,totalsynthesisoftenservesasameasureoftheinorganicsynthesis.powerofagivenreaction.Surveysofrelevantapplicationsofenablingreactionsare,therefore,ofimportanceinthatthey[8]notonlyhelptounderscoreth