第5章逆合成分析法

1、主要讲授内容主要讲授内容 FGACO2HOCH3OFridel - CraftsOCH3OOOPhO COOHPhPhMgBrO COOHOOO重接Phor重接FGAPhOHPhMgBrO合成子试剂 CHO OHPPh3OHC OHWittig 重接OOHOHC OHFGIOO BayerVilligerOFGAOCOOEt COOEt OEtO 重接FGICOXXOCDielsAlderOOO CH2CH2CH3COHHCH2CH2CH3COHHabCOHHCH2 CH2 CH3a1 1a aCH2CH2CH3COHHPhMgBrCOCH2CH2CH3H2 2a aCH2CH2CH3COHH

2、COHHCH2 CH2 CH3bCOCH2CH2CH3NaBH4COCH2CH2CH3c c合成子合成子CH2CH2CH3COCH2CH2CH3COClMgBrHCCH2CH2CH3OEt2OCOMgBrHCH2 CH2 CH3NH4ClH2OCOHHCH2 CH2 CH3CH3CH2CH2COOHSOCl2CH3CH2CH2COClC6H6AlCl3COCH2CH2CH3NaBH4CH3OHCOHHCH2 CH2 CH3 b badis bdis aCH3OHCH3OCH3OHcdH3CCH3MgIMgBrBrOHCH3OHCH3OCH3CH3COOHFGIFGAbac COOEt COOE

3、t MgBrCO2 BrFGI OH MgBr CHO MgBr CHOdis cdis bFGICOOEtCOOEt Brdis bdis c BrCOOEtdis c Br COOEt COOEtdis b Br COOEt COOEtdis aDACOOMeCOOMeCOOMeor Lewis acidCOOMedisCHOCHOH2NMeOCH3CH3ONMeNROdisOH2NRCH2OCH2OOF FG G A AO OHO OHOOOOOOOOMeONaMeOHO HC XX XOXCXX = OR, NHR, SR 等OHCOOH OOOCOOHCH2(CO2Et)2(1) E

4、tONa(2) nC7H15Br(CO2Et)2CHC7H15n(2) O(1) EtONaOOEtO2C (1) HO, H2O(2) H , OO dis aOOXdis bOOXOba (CH3CO)2OAlCl3COCH3EtMgBrEt2OH3OC CH2CH3CH3OHCl2ClMgEt2OMgClCH3COCH3H3OCCH3CH3OHB B r rM M g gT T H H F FM M g gB B r rC C O O O O E E t tC C O O O O E E t tH H3 3O OT T H H F FC C O O H HBrMgTHFMgBrOH3OOHHBrBr () OOdisHOHO+OFGIOHHOdisHCCH+2 HCHOOHHOHCCH+OH2 HCHOH2Pd / BaSO4HOHOHClOOO作业作业： 由逆合成分析法，推导下列化合物的合成路线。由逆合成分析法，推导下列化合物的合成路线。()：( ) ()OdisOOdisO+OClONHNOClNOH3OOO:BOCH2=CHCOCH3CH3COCH2COOEtNaOC2H5 ()亲核合成子的亲