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1、SCIENCECHINAChemistry•MINIREVIEWS•July2014Vol.57No.7:926–929doi:10.1007/s11426-014-5144-5RecentadvancesofintermolecularDiels–Alderreactioninbio-inspiredsynthesisofnaturalproducts1,2†2†1*2*2*WANChunYun,DENGJun,LIUHua,BIANMing&LIAng1SchoolofPharmacy,JiangxiUniversityofTradit
2、ionalChineseMedicine,Nanchang330004,China2StateKeyLaboratoryofBioorganicandNaturalProductsChemistry,ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciences,Shanghai200032,ChinaReceivedMay4,2014;acceptedMay20,2014;publishedonlineJune3,2014TheDiels–Alder(D–A)reactioniso
3、neofthemostpowerfulreactionsinorganicsynthesis.TheintermolecularD–Areactionattractsmuchlessattentionsthanitsintramolecularcounterpartinnaturalproductsynthesis,possiblyduetotheissuesofreac-tivityandselectivity.Inthepastdecade,theintermolecularD–Areactionhasbeenincreasinglyu
4、tilizedinthetotalsynthesisofstructurallycomplexnaturalproducts.Inthisarticle,wepresentafewexamplesfortheelegantapplicationsoftheintermolec-ularD–Areactionthatareinspiredbybiosynthetichypothesesofthetargetnaturalproducts.TheseexamplesdemonstratethatD–Areactionisnotonlyusefu
5、lforpreparingbuildingblocksbutalsopowerfulforcouplingstructurallycomplicatedandste-ricallydemandingsegmentsinahighlychemo-andstereo-controlledfashion,whichmayinspirefurtherdevelopmentsofin-termolecularD–Areactionfrombothstrategyandmethodologyperspectives.intermolecularDiel
6、s–Alderreaction,bio-inspiredsynthesis,dimerization,terpenoid1Introductioncationsintotalsynthesis.ThisarticlehighlightssomeofsuchexamplesthathavenotbeenincludedinthepreviousTheDiels–Alder(D–A)reactionisausefultoolinorganicreviews[1–9].synthesis.Itspowerhasbeendemonstratedin
7、theformationofC–Cbonds,constructionofquaternarycenters,assembly2Selectedrecentexamplesofintermolecularofringsystems,andcontrolofstereochemistry.AlthoughDiels–Alderreactioninbio-inspiredsynthesisofD–Areactionwasinitiallydiscoveredinanintermolecularmanner,intramolecularD–Are
8、actionattractsmoreatten-naturalproductstionsinbothmethodologydevelopmentandcomplex2.1Tota
