1: 1.) 1 molpercent OsO4; 2.) TsOH / 1.) THF, acetone; 2: 1.) KOH; 2.)dicyclohexylcarbodiimide, Me2SO, trifluoroacetic acid, pyridine / 1.) MeOH; 2.) benzene 4: 1.) copper(I) iodide, tributylphosphine; 2.) HMPA / 1.) THF, -78 deg C; 2.) -30 deg C, 3 h 5: 89 percent / aqu. HF, pyridine / acetonitrile 6: 98 percent / Al(Hg) / tetrahydrofuran; H2O 7: enzyme View Scheme

Novosyme sp 435 lipase in various solvent(s) T=20°C; pH=8; 18 h;

sodium hydroxide; Esterase(porcine liver)PLE in water T=32°C; 8 h; further enzymes; pH=7, phosphate buffer; Product distribution;

potassium hydroxide; pig pancreatic lipase T=37°C; 8 h; 0.1 M phosphate buffer (pH 7); Yield given. Yields of byproduct given;

sodium hydroxide; phosphate buffer; immobilized porcine liver esterase (PLE, E. C. 3.1.1.1) on Eupergit C T=32°C; 14 h; pH= 7;

sodium hydroxide; Esterase(porcine liver)PLE in water T=32°C; 8 h; further enzymes; pH=7, phosphate buffer; Product distribution;

potassium carbonate in methanol T=0°C; 4 h;

1: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 2: 99 percent / p-toluenesulfonic acid hydrate / 60 h 3: 99 percent / KOH / methanol / 0.5 h 4: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 5: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 6: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 7: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 2: 99 percent / p-toluenesulfonic acid hydrate / 60 h 3: 99 percent / KOH / methanol / 0.5 h 4: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 5: 1.) n-BuLi, triphenylmethane / 1.) hexane-THF, 0 deg C, 15 min; 2.) hexane-THF, -78 deg C,15 min 6: 97 percent / silica gel / toluene / 9 h / Heating View Scheme

1.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 2.2: 22 h / 25 - 30 °C / Inert atmosphere 3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 4.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 5.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme