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《Synthetic approaches to adriamycin. 2. Degradation of daunorubicin to a nonasymmetric tetracyclic ketone and refunctionalization of the A ring to adriamycin 》由会员上传分享，免费在线阅读，更多相关内容在学术论文-天天文库。
1、SyntheticApproachestoAdriamycinJ.Org.Chem.,Vol.42,No.23,19773653(3)L.NoverandM.Lucknsr,Biochem.Physiol.Pflanzen,168,293(1974).beenputforwardastheself-condensatlonproductofanthranilicacidLA.(4)E.A.AboutablandM.I-uckner,Phytochemistry,14,2573(1975).Chat
2、terjeeandM.Ganguly,J.Org.Chem.,33,3358(1966)],whichis(5)I.Luft,Pharrnazie,29,73(1974);I.RichterandM.Luckner,Fhytcchemistry,clearlyinconsistentwithourdata.Whileimayrepresentanalternatemode15,67(1976).ofself-condensationofanthranilicacid,noevidenceforit
3、sformationwas(6)(a)J.D.White,W.EHaefliger,andM.J.Dimsdale,Tetrahedron,26,233adducedinthepresentwork.(1970);(b)P.K.Martin,H.Rapoport,H.W.Smith,andJ.L.Wong,J.Org.(9)G.A.ArcherandL.H.Sternbach,Chem.Rev.,68,747(1968).Chem.,34,1359(1969).(IO)T.A.Geissmanan
4、dD.H.G.Crout,"OrganicChemistryofSecondaryPlant(7)E.G.BreitholleandC.H.Stammer,J.Org.Chem.,41,1344(1976),andMetabolism",Freeman,CooperandCo.,SanFrancisco,Calif.,1969,ppreferencescitedtherein.435-439.(8)M.Kurihara,Makromol.Chem.,105,84(1967).Adifferents
5、tructure(i)has(11)Inthisview,theenzymaticinterconversionof3and4isareversiblesidereaction,tangentialtothemainpathwayleadingto1.(12)G.W.KirbyandS.Narayanaswami,J.Cherrt.SOC.,ferkinTrans.1,1564(1976).(13)H.M.R.Hoffmann,Angew.Chem.,lnt.Ed.Engl.,8,556(1969
6、).(14)S.C.Pakrashi,J.Bhattacharyya,L.F.Johnson,andH.Budzikiewicz,Tet-rahedron,19,1011(1963).(15)H.Newman,J.Org.Chem.,30,1287(1965).(16)S.C.PakrashiandJ.Bhattacharyya,Tetrahedron,24,1(1968).(17)W.E.NolandandD.A.Jones,J.Org.Chem.,27,341(1962).SyntheticA
7、pproachestoAdriamycin.2.DegradationofDaunorubicintoaNonasymmetricTetracyclicKetoneandRefunctionalizationoftheARingtoAdriamycinThomasH.Smith,*AllanN.Fujiwara,WilliamW.Lee,HelenY.Wu,andDavidW.HenryBio-OrganicChemistryDepartment,StanfordResearchInstitute
8、,MenloPark,California94025ReceivedMay16,1977Asynthesisofadriamycin(2)viaelaborationofthefunctionalitiesatthe7and9positionsofthenonsymmetrictetracyclicketone5isdescribed.Daunorubicin(1)wasdegradedinhighyieldto5byathree-stepprocedure.Addi-tionof
