1.1: NaHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C 1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 1.3: diethyl ether; tetrahydrofuran / -100 - 20 °C 2.1: Bu4NF*3H2O / tetrahydrofuran / 20 °C / overnight View Scheme

1: 39 mg / MnO2 / tetrahydrofuran / 6 h / Ambient temperature 3: 5percent sodium amalgam / tetrahydrofuran; methanol / 9 h / -20 - 20 °C 4: n-Bu4NF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min 2: 1.) n-butyllithium, 2.) 5percent H2O2 / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min View Scheme

N-chloro-succinimide; dimethylsulfide 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min;