1: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent 2: 95 percent / Ca(BH4)2 / tetrahydrofuran 3: NaOMe / methanol / Ambient temperature; e.e. 90percent View Scheme

1: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent 2: 95 percent / Ca(BH4)2 / tetrahydrofuran 3: 67 percent / NaOMe / methanol / Ambient temperature; e.e. 90percent View Scheme

Multi-step reaction with 2 steps 1: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent2: LiCl