phosphate buffer in ethanol T=27°C; the fungus Cunninghamella echinulata NRRL 3655, in fermentor 450 rpm, 30 L/h air;

phosphate buffer in ethanol NADPH-dependent monooxygenase from Pseudomonas putida NCIMB 10007 presence; Title compound not separated from byproducts;

1: 80 percent / 18-crown-6 / acetonitrile / 3 h / 60 °C 2: 72 percent / AcCl / ethanol / 4 h / 50 °C 3: 60 percent / TFA / CH2Cl2; cyclohexane 4: sachharose / baker' yeast View Scheme

1: 60 percent / TFA / CH2Cl2; cyclohexane 2: sachharose / baker' yeast View Scheme

1: H2 / Pd/C / diethyl ether / 24 h 2: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 3: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 4: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 5: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux View Scheme

1: 95 percent / LAH / tetrahydrofuran / 0 deg C to reflux 2: 95 percent / DMAP, Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / Et3N / dioxane / 12 h / Heating 4: 95 percent / H2 / Pd/C / methanol / 24 h View Scheme

1: 95 percent / LAH / tetrahydrofuran / 0 deg C to reflux 2: 95 percent / DMAP, Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / Et3N / dioxane / 12 h / Heating 4: 95 percent / H2 / Pd/C / methanol / 24 h 5: 95 percent / H2 / Pd/C / ethanol / 24 h 6: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C View Scheme

1: H2 / Pd/C / diethyl ether / 24 h 2: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 3: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 4: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 5: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 6: 95 percent / H2 / Pd/C / ethanol / 24 h 7: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C View Scheme

1: H2 / Pd/C / diethyl ether / 24 h 2: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 3: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 4: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 5: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 6: 95 percent / H2 / Pd/C / ethanol / 24 h 7: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 8: 90 percent / CrO3 / acetone / 0 °C View Scheme

1: 95 percent / LAH / tetrahydrofuran / 0 deg C to reflux 2: 95 percent / DMAP, Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / Et3N / dioxane / 12 h / Heating 4: 95 percent / H2 / Pd/C / methanol / 24 h 5: 95 percent / H2 / Pd/C / ethanol / 24 h 6: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 7: 90 percent / CrO3 / acetone / 0 °C View Scheme