1.1: Ti(O-i-Pr)4; t-BuOOH; D-(-)-DIPT / CH2Cl2 / 16 h / -15 °C 1.2: Me2S / CH2Cl2 / 0.5 h / -15 °C 1.3: 38 percent / tartaric acid; NaF / CH2Cl2; H2O; diethyl ether / 2 h / 20 °C 2.1: 98 percent / DMAP; CSA; DCC / CH2Cl2 / 20 °C 3.1: 73 percent / TBAF / tetrahydrofuran / 24 h / 0 °C 4.1: 92 percent / DMAP; DCC; CSA / CH2Cl2 / 20 °C 5.1: 70 percent / Zn(BH4)2 / diethyl ether / 1 h / -94 °C 6.1: 88 percent / (i-Pr)2NEt / CH2Cl2 / 16 h / 20 °C 7.1: 93 percent / DDQ / CH2Cl2; H2O / 0.5 h / 20 °C 8.1: NaHCO3; NBS / acetone; H2O / 2 h / -15 °C 8.2: furan; pyridine / acetone; H2O / 20 °C 9.1: NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h / 20 °C 10.1: Cl3C6H2COCl; Et3N / tetrahydrofuran / 2 h / 20 °C 10.2: 55 mg / DMAP / toluene / 5 h / 40 °C 11.1: 92 percent / CF3CO2H / CH2Cl2 / 1.5 h / 20 °C 12.1: NaBH4 / methanol / 1 h / 0 °C View Scheme

1: 90 percent / NaHCO3; NaOAc*3H2O; NBS / tetrahydrofuran; H2O / 1 h / 0 °C 2: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C 3: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 4: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 5: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 6: 86 percent / DMAP; pyridine / CH2Cl2 / 0 °C 7: 86 percent / H2 / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C View Scheme

1.1: 90 percent / NaHCO3; NaOAc*3H2O; NBS / tetrahydrofuran; H2O / 1 h / 0 °C 2.1: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C 3.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 4.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 5.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C 6.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 7.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C 7.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C 8.1: 62 percent / DBU / toluene / 1 h / 0 °C 9.1: 91 percent / DBU / toluene / 1 h / 0 °C View Scheme

chlorine in tetrahydrofuran; water T=-10°C; 0.5 h; Yield given. Yields of byproduct given;

chlorine in tetrahydrofuran; water T=-10°C; 0.5 h; Yield given. Yields of byproduct given;

tert-butylhypochlorite in acetic acid T=0 - 25°C; Yields of byproduct given;

Pseudomonas cepacia lipase; 4 A molecular sieve; peracetylated-β-cyclodextrin in toluene T=40°C; 8 h; Title compound not separated from byproducts;

Pseudomonas fluorescence Amano AKG lipase in cyclohexane T=36°C; 2 h;

Lipase PS Amano from Burkholderia cepacia in di-isopropyl ether T=25°C; 24 h; Resolution of racemateIonic liquidsolid phase reactionEnzymatic reaction; optical yield given as percent ee;

Pseudomonas cepacia lipase; peracetylated-β-cyclodextrin in toluene T=40°C; 8 h; Product distribution; Further Variations:Solventstimes;