1: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 2: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 3: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 4: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 5: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 6: 82 percent / dimethylformamide / Ambient temperature; overnight 7: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 8: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 2: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 3: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 4: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 5: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 6: 82 percent / dimethylformamide / Ambient temperature; overnight 7: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 8: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: SOCl2, Py / diethyl ether / -10 °C 2: (i) Mg, I2, Et2O, (ii) /BRN= 1900390/ View Scheme

air; NADH-H+; Fe2S2 ferredoxin from Pseudomonas species NCIB 9816-4; α3β3 oxygenase from Pseudomonas NCIB 9816-4; reductase from Pseudomonas species NCIB 9816-4 in water T=23°C; pH=6.9; 0.5 h;

lithium aluminium tetrahydride in diethyl ether T=0°C; 0.5 h;

dimethylaluminum chloride in dichloromethane T=25°C; 1 h;

1: 1) magnesium / 1) THF, -12 to -7 deg C, 1 h, 2) to room temperature, overnight 2: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C View Scheme

lithium aluminium tetrahydride

potassium hydroxide in diethylene glycol T=150°C;

NADH-H+; phenyl-methyl-sulfonyl fluoride; DL-threo-1,4-dimercapto-2,3-butanediol in phosphate buffer T=37°C; pH=7.4; 2 h; Product distribution; Further Variations:ReagentsSolventspH-values;