有机习题福山组会题fukuyama题2007-3.docxVIP

FukuyamaGroup-GroupMeetingCumulativeExamination11/01/20071.1)NaH(1.1eq),THF-DMF;homoallylbromide,72%[Cu(PPh?)Cl]?EIO?C-ROPh“仓2)hv(300nm),benzene81%?THFreflux89%*1.7:1mixtureoftwodiastereomers(Themajordiastereomerwasusedinthenextstep.)0D.StC.Blacketal.,Synthesis,1981(2006)2.H.1)H(C??H?O?)tBuCOU,THF,-78℃?0000C??H??O?2)DDQ,benzene,reflux1,2-dichlorobenzenereflux83%for3stepsC??H??O?D.Maletal.,Chem.Commun.,1181(1996)3.1)Cl?COCl,Zn(Cu)Et?O,reflux2)Zn,AcOH2.3)HF,MeCN-H?O,20℃4)CSA,hexane-CH?Cl?,△演習で学ぶ有機反応機構C068(化学同人)E.Vedejsetal.J.Org.Chem.,49,184