in tetrahydrofuran; diethyl ether T=-78°C; 0.166667 h;

1: 1) NCS, 2) silica gel / 1) CCl4, 50 deg C, 4.5 h, 2) EtOAc, 16 h 2: 71 percent / diethyl ether; tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 65 percent / Ac2O, MeSO3H / CH2Cl2 / 192 h / Ambient temperature 2: 71 percent / diethyl ether; tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 1.) BuLi, TMEDA / 1.) THF 2: 74 percent / MCPBA / CH2Cl2; tetrahydrofuran / -78 °C 3: 65 percent / Ac2O, MsOH / CH2Cl2 / 192 h / 25 °C 4: 2) NH4Cl / 1) THF, Et2O, -18 deg C, 15 min; 2) H2O, room temp., 18 h View Scheme

ammonium chloride 1) THF, Et2O, -18 deg C, 15 min; 2) H2O, room temp., 18 h; Yield given. Multistep reaction;

(i) nBuLi, tetra-N-methyl-ethane-1,2-diamine, (ii) /BRN= 639794/; Multistep reaction;