hydrogen; acetic acid; Rh/Al2O3 in methanol P=2280 Torr; 10 h;

triethylamine; bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane in tetrahydrofuran 1.) -20 deg C, 5 min; 2.) -20 deg C, then 0 deg C, 3 h;

1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C 2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h 3: 90 percent / pyridine / pyridine / 48 h / 23 °C 4: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 5: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 6: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h 2: 90 percent / pyridine / pyridine / 48 h / 23 °C 3: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 4: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 5: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 2: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 3: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 90 percent / pyridine / pyridine / 48 h / 23 °C 2: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 3: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 4: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, 2.) THF, 23 deg C, 16 h 2: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C 3: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h 4: 90 percent / pyridine / pyridine / 48 h / 23 °C 5: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 6: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 7: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 2: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

sodium hydroxide; jones reagent 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h; Yield given. Multistep reaction;