1: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase 2: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h 3: 1.) n-butyllithium, 2.) BF3*OEt2 / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1.5 h 4: 92 percent / H2, quinoline / Lindlar catalyst / ethyl acetate / 760 Torr 5: 89 percent / p-TsOH, water / toluene / 1.5 h / Heating View Scheme

1: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase 2: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h View Scheme

2: 99 percent / K2CO3, H2O / methanol / 12 h / Ambient temperature 3: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h View Scheme