1: 1.) CuI / 1.) Et2O 2: KN(Me4Si)2 / tetrahydrofuran; dimethylformamide View Scheme

KN(Me4Si)2 in tetrahydrofuran; N,N-dimethyl-formamide Yield given;

1: 1.) O3, 2.) (CH3)2S / 1.) MeOH, - 60 deg C 2: CHCl3 / Heating 3: dibal / diethyl ether / -78 - 0 °C View Scheme

dimethylsulfide; ozone 1.) MeOH, - 60 deg C; Yield given. Multistep reaction;

1: 1.) O3, 2.) (CH3)2S / 1.) MeOH, - 60 deg C 2: CHCl3 / Heating 3: dibal / diethyl ether / -78 - 0 °C 4: TEA, DMAP / CH2Cl2 5: I2 / acetonitrile / 0 °C 6: 13 percent / 1.) AgBF4, 2.) H2O / 26.5 h / 60 °C View Scheme