OHN2)KOH,1)KH〈excess)18-crown-6,THf,「tCICO2Me(excess〉pyridine,-78°CtortClClquinoline210°CTBNaOM1)rr)CPBA,CH2CI2,0°C2)QqHBF4,CH2CI2,rt3)B「Mg/、IVle,cecl3THF,-78°Ctort4)PdCI2(MeCN)2(1eq)DME,rtCheat,200°CEtO2C^1)TfOH,CH2CI2,0°Cpyridine2)toluene,reflux3)TBAF,H2O2DMF,55°Ctoluene-30°CtortPh-CO2HPh^NH2MePhiPd(OAc)2(Cat)NaOAc,LiCIDMF,100°Ctoluene110°C—OH+KOHdioxane,rt出0‘PhCI190°CO2Me2)to2)silica1)t-BuOOH,VO(acac)2CH2CI2,-30°C1)NOCIpyridine,o°C2)hvjpyridine3)Tsci,pyridinebenzenesrt1)Me3Si^N2BuLi,DME-hexaneOAC2O85°C1)Rh(OAc)2(cat)CH2CI2)Sm|2THF,50°C1)TSNH2,BF3-Et2Obenzene,reflux1)H2C^CHMgB「THF,-10°C2)DBU,CI3CCNCH2CI2Jrt3)Ca(0CI)2CH2CI2-H2O,10°C4)aqHCITHF-H2O,rt1)EtMgBrTHF-H2O・2)benzene,refluxH2)■\)CO2EtPh3P(cat)benzene,refluxTi(OP「)41)Feci3卜PrMgCI(2eq)pyridine,DMFEt2O2)NaOAc,MeOHTrO3)KOHethyleneglycolreflux1)PhSeBr,i-Pr2NEtMeCN,0°C2)NalO4,NaHCO3MeOH-H2O,rt3)hexylamine,MgSO4toluene,reflux+n-BuLi1)pyrrolidine/to|uene,「ef|uxTMSEtOAcreflux2)AC2O70to125°CHgCl2H20-caetonerefluxAc。纷严oBnoOMeOBn1)LiO-i-Pr(cat)Et2O,rt2)NaoH,MeoHrefluxBF3-Et2OethyleneglycolCH2CI2,20°C1)MeAICI2CHCI3,rt2)NaBH4MeOH,0°C2,6-lutidine3)MSCI,Et3Ntoluene,「tCH2CI2,-78°C4)t-BUOKTHF,refluxPhAsAPh1)CH3CHOEt2O,0°C2)CI2CHOCH3t-BuOLi,Et2O0°Ctort3)H2O2,NaoAcH2O,refluxPhNCMe3snsnMe3hvbenzene20°CPhNEt2230°CMebenzene,reflux；Ho^°oCl『3〜Ru—CH应Ph鬥）benzenert,4hPhMgBrEt2O-78°CtortHn・BuLi,THFn-BuLi（1eq）・78°C;THF,-78°C;1)N3CH2CO2MeNaoH,MeoH,rt2)cydohezane,reflux3)p-Xyiene,reflux2)H2SO4MeOH0°CO-78°CtortOBnMeMeEt2O-78to20°CHgCI2鬥)NBSMeOHCH3CNhvNaBH4MeoH5to10°COHPhl(OCOCF3)2THFrtmesytiiene200°CMeOLDATHF,・80°CTHF-80to30°C(CH2)4CH3MeSm|2HMPAt-BuOHTHF0°C0乂o(Meidum'sacid)H2NCH2CH2NH22ACOH(Cat)Na2S04,MecN,20°CrefluxNaOMeMeOHrefluxt-RUliMen\THF3)(Me2N)3P-78°C1)NaH,Me=CH2BrDMF,60°C2)LiAIH4,AICI3Et2O,0°C3)mcPBA,CH2CI2,rtKCN(excess〉DMF-H2O,50°C1)O=S=N-CO2Mebenzene,0°C2)PhMgBrTHF,-60°C1)LDA?TBSCIHMPA,THF2)O3,CH2CI2?rt3)H2,Pd/C,EtOH,rtbenzene,0°CPh3P=CHCNPhMgBrEDCITHF,-60°CCH2CI2,rt"H2N^BrOMeCO2HAcCItoluene,reflux2）NaBH4,H2SO4EtOH,-30°C3）M€^SiCH2MgCI（2eq）CeCk,THF;aqHCI1）（COCI）2,benzene2）Et3N,toluene,reflux3）MeLi,THF,-78°C4）Mn（OAc3）,CU（OAC）2EtOH,rtPh〜CH。+OOHPhrttorefluxTMSOTf（0-5eq）MS4An-BuLi（1eq）OTf/Me>hLindlarcatalystquinolineCH2CI2-MeOH25°CZn（CU\CI3CCOCIN（BOC）2THF,-45°CPd（OAc1）Pd2（dba）3-CHCI3（25mo|%）DPPE,MECOCH2CO2MeTHF,rti2）silicagelMeClMeAICI3CH2CI20°CMe3SiOHTBSOEtAICI2AdecalinCH2CI2175°C・78°C1)NBS,BaCO3CHCI3,reflux2)activatedZni-PrOH-H2OrefluxDEAD,Ph3PTHF-15°Ctortn-BuLi330°CSiMe32SO2NHNH2Me3SiOH/excess、THF-40°COTiCI4-(THF)2(5)i-Pr2NEtCH2CI2,rt1)Zn/CU\CLCCOCIEt2O,reflux2)Zn,HOAC,85°C3)HF,MeCN-H2O,20°C4)CSA,hexane-CH2CI2A5)Znci2,hvCO,THF6)l2,MeCN;rtOHOHMeMe1)CIOC乂OAC(2°q)MecN2)NaOMe,THF3)mCPBA,CH2CI2)4)MeOH,heat5)H2,Pd/C,MeOHMeLi(cat)Ph2O,180°CTBAF1)NaOH,THF,rt2)Rh2(OAc)4ben》enreflux3)RaneyNi,acetone2)H2C=CHTMSO儿2+4°OHMen-BuLiTHgH^NHOH,NaHgEtOH,rt1)Rh2(OAc”benzene,refluxMe2)BF3-Et2Obenzene?rt1)LiSnMe3,THFO“号BF3-Et2O-78°C2)Pb(0Ac)4,CaCO3benzene,「eflux3)H2,(Ph3P)3RhCI2)ACCI,Et3N,Et2O,0°Ctort3)NaOAc,AcOH,rtOMeCHOMeMe1)o2,hvhvCH2CI2MeOSiMe3+=cTiCI4CH2CI2-75to0°CEtOHPhxMeCH2CI2,rt*^NHTSMeCN,760°CEt2O,rt;SOCI2Et2OH2C=CHCHOrt-10°CtortCO,Pd(PPh3)4K2CO3,n-Bu4NBrX]严Lit-BU0K,THF,rt;refluxMeoOMeClMe1)KHDMSEt2O2)O3,CH2CI2-78°C;Ph3PTSOHbenzeneBnBn_^=c^^CO2HMeoHtoluenertreflux*^NHTSMeCN,7OMesph=4B3tS-BUKOTHF0°CEt2O,rtTHF,rtBoc1)LDA,Et2O0°C2)KH,CS2；Me|THF,0°C3)n-BU3SnH,AIBNtoluene,100°C(HC®N&2SC)4MecNrefluxQPhNaHCO3NiCI2/NaBH4►►Snci4,CH2CI2f-78°CbenzeneEtOH,rtrefluxBnoEt3NBF3-Et2OH2OEt2O-78°Cdioxane0°CEto2c^Tf2OpyridineMeCH2CI2,0°CCH2CI22)benzene,65°C0°CH1)t-BuOK,t-BuOH-5°Ctort2)O3,N8HCO3MeOH-CH2CI2,-70°C3)AC2O,Et3N,DMAPbenzenerefluxMeliiuTMSOTftoluenert1)PhLi,Et2O;H3O+2)TSOH,H2OCH2CI21)Br2)CHCI3Irt2)AgNC)3,M6OHreflux3)TFAA,DMSOCH2CI2-78°CtortN1)NH2OH-HCINaoAcMeoH,rt2)sealedtubetoluene,160°C1)—SPh2^F4KOH,DMSOaqBF4,Et2O,rt2)PhSSPh(excess)NaOMe,MeOH,AOTsMe1)ci-s^c°2Wepyridine,CH2CI22)mcPBA(2eq)CH2CII2CO2t-Bu3)KOMe,THF-MeOH4)sm||2jTHF-MeOHEtOOEtOSiMe3BF3-Et2OCH2CI2]-75°COSiMe3CH3CO2H-75°CtortMerAH°3)(HCHO)niMS4Ato|uene「ef|ux4)MeoSO2F,ether,0°CLiAlH4,THF,rt1)NH2OH-HCINaOAc,IVleOH；rt2)NaBH3CN,M^OH,「t
