1: Pseudomonas cepacia lipase 2: Et3N / tetrahydrofuran / 2 h / 0 - 25 °C 3: dimethylsulfoxide / 12 h / 45 °C 4: aq. H2SO4 / acetic acid / 2 h / 110 °C 5: 1.) LDA, HMPA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 deg C to 0 deg C 6: BBr3 / CH2Cl2 / 13 h / -18 - 0 °C View Scheme

lithium aluminium tetrahydride in diethyl ether 2 h; Ambient temperature;

1: 1.) C2H5ONa / 1.) ethanol, 2.) ethanol a) RT, overnight, b) reflux, 8 h 2: 79 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature View Scheme

1: NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C 2: dimethylsulfoxide / 50 °C 3: H2SO4 / acetic acid; H2O / 0.5 h / 110 °C 4: 1) diisopropylamine-Li / 1) THF/HMPA, -70 deg C, 2) THF/HMPA, -70 to -50 deg C 5: 80 percent / BBr3 / CH2Cl2 / 0 °C / demethylation 6: LiAlH4 / tetrahydrofuran / 2 h / 20 °C View Scheme

1: NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C 2: dimethylsulfoxide / 50 °C 3: H2SO4 / acetic acid; H2O / 0.5 h / 110 °C 4: 1) diisopropylamine-Li / 1) THF/HMPA, -70 deg C, 2) THF/HMPA, -70 to -50 deg C 5: 80 percent / BBr3 / CH2Cl2 / 0 °C / demethylation 6: LiAlH4 / tetrahydrofuran / 2 h / 20 °C View Scheme