NH NH3 HCI (CH2)8 NH (CH2)B NH CI (CH2)8 NH 6-B4 Octanal aus N-Formylpiperidin und dem Grignardreagenz aus 1-Bromoctan(2-Al) Hept、Br 1)Mg, EtO Hept 6-B4
O Cl (CH2 )8 Cl O NH3 O Cl (CH2 )8 Cl O NH3 O Cl (CH2 )8 NH3 O Cl O Cl (CH2 )8 NH2 O O H2N (CH2 )8 NH2 O analog - HCl 6-B4 Octanal aus N-Formylpiperidin und dem Grignardreagenz aus 1-Bromoctan (2-A1) 1) Mg, Et2O 2) Hept Br Hept O O N 6-B4
Mg Hept、MgBr (SET) gbR H Hept、MgBt He N ⊙ Hept Hept 6-c1 Acety lsalicylsaure aus salicylsaure CO,H H2SO OAC 6-C1
Hept Br Mg (SET) Hept MgBr Hept MgBr O N N Hept O H MgBr NH Hept O H MgBr H Hept O - HN 6-C1 Acetylsalicylsäure aus Salicylsäure CO2H OH CO2H OAc O O O H2SO4 6-C1
cO, CO2H CO,H CO2H OAc HOAC 0:H 6-C1 6-C2 Sebacinsauremonomethylester aus Sebacinsauresauredimethylester 6-C3 10-Methy1-10-hydroxy-undecansaure aus Sebacinsauremonomethylester(6C2) 6-C4 Sebacinsaureethylmethylester aus Sebacinsauremonomethylester( 6-C2 1)Ba(Oh) Meo (CH2)8 OMe 2)H:Oo Meo (CH2)B OH 6-C2 OH O 1)MeMel (CH2)8 OH 2)NH4CI/H,O 6-C3 1)CI-CO-OEt Meo (CH2)8 OEt 2)EtoH
CO2H OH HO O O CO2H O H O O O ~H CO2H O O O O - HOAc H CO2H OAc 6-C1 6-C2 Sebacinsäuremonomethylester aus Sebacinsäuresäuredimethylester 6-C3 10-Methyl-10-hydroxy-undecansäure aus Sebacinsäuremonomethylester (6 C2) 6-C4 Sebacinsäureethylmethylester aus Sebacinsäuremonomethylester (6-C2) O MeO (CH2 )8 OH O O MeO (CH2 )8 OMe O 1) Ba(OH)2 2) H3O 1) MeMgI OH (CH2 )8 OH O 1) Cl-CO-OEt 2) EtOH O MeO (CH2 )8 OEt O 2) NH4Cl/H2O 6-C2 6-C3 6-C4
OH Meo (CH2)8 OMe Meo home Meo (CH2)&OH Meo (CH2)8 OH 6-C2 o: Mgl Me-Mgl (CH2)8 OMe CH4 (CH2)8 OMe 6-C2 Me -Mgl +NH4
O MeO (CH2 )8 OMe O OH O MeO (CH2 )8 OMe O OH O MeO (CH2 )8 O OH + OMe O MeO (CH2 )8 O O -HOMe +H O MeO (CH2 )8 OH O 6-C2 O O (CH2 )8 OMe O 6-C2 Me MgI O O (CH2 )8 OMe O MgI +NH4 / -NH3 H Me MgI -CH4
Mgl (CH2)8 HOMe ( CH2)8 COMe H Me—Mgl OH +Net MeO′(HzC) OH NETs MeO(H2C) Cl\ OEt MeO(H2C) O OEt MeO(H2C)
O O (CH2 )8 OMe O MgI H -HOMe O O (CH2 )8 O Me MgI O O (CH2 )8 O H OH (CH2 )8 OH O 6-C3 O MeO (H2C)8 OH O 6-C2 + NEt3 - HNEt3 O MeO (H2C)8 O O O Cl OEt O MeO (H2C)8 O O O Cl O Et O MeO (H2C)8 O O O OEt Cl