hydrogen; platinum(IV) oxide T=150°C; 18 h; ethyl palmitate;

1: acetonitrile 2: 1) NaCH2SOMe / 1) DMSO, 2) ether 3: C7H7SO3H, H2O 4: 1) NaCH2SOMe / 1) DMSO, 2) ether 5: C7H7SO3H, H2O 6: 1) NaCH2SOMe / 1) DMSO, 2) ether 7: lithium triethylborohydride 8: H2, ethyl palmitate / 150 °C View Scheme

lithium triethylborohydride in tetrahydrofuran T=20°C; 0.25 h;

1: 1) NaCH2SOMe / 1) DMSO, 2) ether 2: C7H7SO3H, H2O 3: 1) NaCH2SOMe / 1) DMSO, 2) ether 4: C7H7SO3H, H2O 5: 1) NaCH2SOMe / 1) DMSO, 2) ether 6: lithium triethylborohydride 7: H2, ethyl palmitate / 150 °C View Scheme

nickel in cyclohexane 2 h; Heating;

1: lithium triethylborohydride 2: H2, ethyl palmitate / 150 °C View Scheme

1: 1) NaCH2SOMe / 1) DMSO, 2) ether 2: C7H7SO3H, H2O 3: 1) NaCH2SOMe / 1) DMSO, 2) ether 4: lithium triethylborohydride 5: H2, ethyl palmitate / 150 °C View Scheme

1: 1) NaCH2SOMe / 1) DMSO, 2) ether 2: lithium triethylborohydride 3: H2, ethyl palmitate / 150 °C View Scheme

1: dimsylsodium, toluene-p-sulphonic acid/silica gel / light petroleum 2: 97 percent / toluene-p-sulphonic acid/silica gel / H2O; tetrahydrothiophene 1,1-dioxide; CH2Cl2 3: 850 mg / diethyl ether / 60 h 4: 64 percent / lithium triethylborohydride / tetrahydrofuran / 0.25 h / 20 °C 5: 61 percent / H2 / platinum oxide / 18 h / 150 °C / ethyl palmitate View Scheme

1: 850 mg / diethyl ether / 60 h 2: 64 percent / lithium triethylborohydride / tetrahydrofuran / 0.25 h / 20 °C 3: 61 percent / H2 / platinum oxide / 18 h / 150 °C / ethyl palmitate View Scheme