1: 1) KOH / 1) THF, MeOH, reflux, 5 h, 2) r.t., 2 h 2: 1) Ti(i-PrO)4, (+)-diethyltartrate, 2) t-butylhydroperoxide / 1) 1,2-dichloroethane, r.t., 10 min, 2) -20 deg C, 16 h 3: 1) I2, PPh3, 2) NaI / 1) CH3CN, r.t., 5 min, 2) reflux, 1 h 4: 11 percent / NaSMe / hexamethylphosphoric acid triamide / 3 h / 100 °C View Scheme

1: 1) I2, PPh3, 2) NaI / 1) CH3CN, r.t., 5 min, 2) reflux, 1 h 2: 11 percent / NaSMe / hexamethylphosphoric acid triamide / 3 h / 100 °C View Scheme

tert.-butyl lithium; sulfur 1) THF, dry ice/acetone bath, 4h, 2) 25 deg C, 0.5h; Yield given. Multistep reaction. Yields of byproduct given;

T=250°C; Newmann-Kwart thermo-rearrangement;

1.1: 78 percent / i-PrMgBr / Ni(acac)2 / tetrahydrofuran; diethyl ether / 9 h / Heating 2.1: 100 percent / K2CO3 / acetone / 12 h / 20 °C 3.1: 77 percent / m-chloroperbenzoic acid / CH2Cl2 / 4.5 h / 0 °C 4.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.58 h / 20 °C 4.2: 83 percent / iodine / tetrahydrofuran; diethyl ether / 6 h / 20 °C View Scheme