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1、LETTER1051StereoselectiveSynthesisof(+)-PaeonilideandConfirmationofitsAbsoluteConfigurationStereoselectiveSynthesisof(+)-PaeonilideChenyingWang,a,bHongbinZhang,*bJikaiLiu,aYanhuaJi,bZhihuiShao,bLiangLibaStateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina,Kunming
2、InstituteofBotany,ChineseAcademyofSciences,Kunming,Yunnan650204,GraduateSchoolofChineseAcademyofScience,Beijing100039,P.R.ofChinabKeyLaboratoryofMedicinalChemistryforNaturalResource,MinistryofEducation,SchoolofPharmacy,YunnanUniversity,Kunming,Yunnan650091,P.R.ofChinaFax+8
3、6(871)5035538;E-mail:zhanghb@ynu.edu.cnReceived8January2006RHAbstract:Thefirstdiastereoselectivesynthesisofpaeonilide,aOHOnovelanti-PAF-activemonoterpenoid,startingfromR-(–)-carvoneHOOwasreported.TheabsoluteconfigurationforpaeonilidewasalsoHOOOestablished.OHHKeywords:diast
4、ereoselectivesynthesis,(+)-paeonilide,absolutePaeonilactoneA,R=Hconfiguration,monoterpenoid,carvonePaeonilactoneBPaeonilactoneC,R=OBzHOOPaeoniarootbark,‘mu-dan-pi’or‘dan-pi’inChinese,isoneofthemostimportantherbaldrugsusedintraditionalOOOPaeonilideChinesemedicine.Representa
5、tivechemicalconstituentsOisolatedfromdifferentspeciesofPaeoniaareanumberofstructurallyrelatedmonoterpenesthatfeaturewithahigh-lyoxygenatedcyclohexanenucleus(Figure1).1In2000,anovelmonoterpenoid,namedpaeonilide,wasisolatedFigure1Examplesoftetrahydrofurancontainingnaturalpro
6、ducts.fromtherootsofPaeoniadelavayi.2ItsnewskeletonwasestablishedbyacombinationofspectroscopicandX-raythusinvestigated.Startingfrom(R)-(–)-carvone,acrystallographicanalysis.Thebioassayindicatedthatpae-brominationreactionwascarriedoutwithNBSfollowingonilideselectivelyinhibi
7、tedtheplateletaggregationin-4aliteratureprocedure.Theallylicbromide5wasthenducedbyPAF(theplateletactivatingfactor)withanIC50subjectedtoanS2substitutionwithsilveracetateinNvalueof8mg/mL,withnoinhibitoryeffectonADP-or5aceticacidtogiveanallylicacetate6.LuchereductionAA-induce
8、dplateletaggregation.DuetoitsimportantwithsodiumborohydrideandfollowingbyMCPBAbiologicala
